Could sodium in ethanol reduce amides to amines?Reduction of α,β-unsaturated nitro compoundsHow to convert benzamide to benzylamine?How can an aromatic ketone be reduced in the presence of a nitro group?Why NaBH4 does not reduce carboxylic acid while LiAlH4 does?What are reducing sugars?Functional difference of Benedict's solution and Fehling's solutionCan HI/P reduction be used to reduce nitroalkanes and nitroarenes to alkyl amines and aryl amines?Do alkyl halides get reduced with hydrogen/nickel catalyst?Are there any reducing agents for reduction of nitrobenzene to aniline other than Sn/HCl?Which functional groups are not reduced by DIBAL.H?
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Could sodium in ethanol reduce amides to amines?
Reduction of α,β-unsaturated nitro compoundsHow to convert benzamide to benzylamine?How can an aromatic ketone be reduced in the presence of a nitro group?Why NaBH4 does not reduce carboxylic acid while LiAlH4 does?What are reducing sugars?Functional difference of Benedict's solution and Fehling's solutionCan HI/P reduction be used to reduce nitroalkanes and nitroarenes to alkyl amines and aryl amines?Do alkyl halides get reduced with hydrogen/nickel catalyst?Are there any reducing agents for reduction of nitrobenzene to aniline other than Sn/HCl?Which functional groups are not reduced by DIBAL.H?
$begingroup$
Strong reducing agents like $ceLiAlH4$ can reduce amides to amines. Sodium in ethanol (as a source of protons) is also a very strong reducing agent. Could it be therefore used to, for example, turn formamide into methylamine?
organic-chemistry organic-reduction
edited 1 hour ago
andselisk♦
21.3k772139
asked 5 hours ago
Francis L.Francis L.
1274
$endgroup$
add a comment |
$begingroup$
Strong reducing agents like $ceLiAlH4$ can reduce amides to amines. Sodium in ethanol (as a source of protons) is also a very strong reducing agent. Could it be therefore used to, for example, turn formamide into methylamine?
organic-chemistry organic-reduction
edited 1 hour ago
andselisk♦
21.3k772139
asked 5 hours ago
Francis L.Francis L.
1274
$endgroup$
add a comment |
$begingroup$
Strong reducing agents like $ceLiAlH4$ can reduce amides to amines. Sodium in ethanol (as a source of protons) is also a very strong reducing agent. Could it be therefore used to, for example, turn formamide into methylamine?
organic-chemistry organic-reduction
edited 1 hour ago
andselisk♦
21.3k772139
asked 5 hours ago
Francis L.Francis L.
1274
$endgroup$
Strong reducing agents like $ceLiAlH4$ can reduce amides to amines. Sodium in ethanol (as a source of protons) is also a very strong reducing agent. Could it be therefore used to, for example, turn formamide into methylamine?
organic-chemistry organic-reduction
organic-chemistry organic-reduction
edited 1 hour ago
andselisk♦
21.3k772139
asked 5 hours ago
Francis L.Francis L.
1274
edited 1 hour ago
andselisk♦
21.3k772139
asked 5 hours ago
Francis L.Francis L.
1274
edited 1 hour ago
andselisk♦
21.3k772139
edited 1 hour ago
andselisk♦
21.3k772139
edited 1 hour ago
andselisk♦
21.3k772139
21.3k772139
asked 5 hours ago
Francis L.Francis L.
1274
asked 5 hours ago
Francis L.Francis L.
1274
asked 5 hours ago
Francis L.Francis L.
1274
1274
add a comment |
add a comment |
1 Answer
1
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oldest
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$begingroup$
Yes, that is used as a pathway for synthesis of amines from amides, albeit rarely.
I quote from the abstract of a communication that reports the same: (emphasis mine)
The reduction of amides to their corresponding amines has been used extensively in the synthesis of many drugs and their intermediates. This reaction has usually been carried out by means of metal hydrides (especially lithium aluminium hydride) or by catalytic hydrogenation over various catalysts. Metal and alcohol has been used for the reduction of ketones to their corresponding hydroxy compounds and oximes to their corresponding amines, but the reduction of amides under these conditions, although previously reported, is not well documented in major works of organic chemistry. This procedure is specially useful for industry since it is safer, less expensive, requires less time and provides higher yields (65-80 per cent) when compared with lithium aluminium hydride or catalytic reduction methods.
The emphasized text is written in a slightly confusing language but nonetheless confirms that amides can be reduced to amines using $ceNa/ROH$, otherwise known as Bouveault-Blanc reduction.
References:
Bhandari, K. , Sharma, V. L. and Chatterjee, S. K. (1991), ChemInform Abstract: A Convenient Method for the Reduction of Amides to Their Corresponding Amines.. ChemInform, 22: no-no. DOI: 10.1002/chin.199118077
answered 1 hour ago
William R. EbenezerWilliam R. Ebenezer
1,243422
$endgroup$
add a comment |
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$begingroup$
Yes, that is used as a pathway for synthesis of amines from amides, albeit rarely.
I quote from the abstract of a communication that reports the same: (emphasis mine)
The reduction of amides to their corresponding amines has been used extensively in the synthesis of many drugs and their intermediates. This reaction has usually been carried out by means of metal hydrides (especially lithium aluminium hydride) or by catalytic hydrogenation over various catalysts. Metal and alcohol has been used for the reduction of ketones to their corresponding hydroxy compounds and oximes to their corresponding amines, but the reduction of amides under these conditions, although previously reported, is not well documented in major works of organic chemistry. This procedure is specially useful for industry since it is safer, less expensive, requires less time and provides higher yields (65-80 per cent) when compared with lithium aluminium hydride or catalytic reduction methods.
The emphasized text is written in a slightly confusing language but nonetheless confirms that amides can be reduced to amines using $ceNa/ROH$, otherwise known as Bouveault-Blanc reduction.
References:
Bhandari, K. , Sharma, V. L. and Chatterjee, S. K. (1991), ChemInform Abstract: A Convenient Method for the Reduction of Amides to Their Corresponding Amines.. ChemInform, 22: no-no. DOI: 10.1002/chin.199118077
answered 1 hour ago
William R. EbenezerWilliam R. Ebenezer
1,243422
$endgroup$
add a comment |
$begingroup$
Yes, that is used as a pathway for synthesis of amines from amides, albeit rarely.
I quote from the abstract of a communication that reports the same: (emphasis mine)
The reduction of amides to their corresponding amines has been used extensively in the synthesis of many drugs and their intermediates. This reaction has usually been carried out by means of metal hydrides (especially lithium aluminium hydride) or by catalytic hydrogenation over various catalysts. Metal and alcohol has been used for the reduction of ketones to their corresponding hydroxy compounds and oximes to their corresponding amines, but the reduction of amides under these conditions, although previously reported, is not well documented in major works of organic chemistry. This procedure is specially useful for industry since it is safer, less expensive, requires less time and provides higher yields (65-80 per cent) when compared with lithium aluminium hydride or catalytic reduction methods.
The emphasized text is written in a slightly confusing language but nonetheless confirms that amides can be reduced to amines using $ceNa/ROH$, otherwise known as Bouveault-Blanc reduction.
References:
Bhandari, K. , Sharma, V. L. and Chatterjee, S. K. (1991), ChemInform Abstract: A Convenient Method for the Reduction of Amides to Their Corresponding Amines.. ChemInform, 22: no-no. DOI: 10.1002/chin.199118077
answered 1 hour ago
William R. EbenezerWilliam R. Ebenezer
1,243422
$endgroup$
add a comment |
$begingroup$
Yes, that is used as a pathway for synthesis of amines from amides, albeit rarely.
I quote from the abstract of a communication that reports the same: (emphasis mine)
The reduction of amides to their corresponding amines has been used extensively in the synthesis of many drugs and their intermediates. This reaction has usually been carried out by means of metal hydrides (especially lithium aluminium hydride) or by catalytic hydrogenation over various catalysts. Metal and alcohol has been used for the reduction of ketones to their corresponding hydroxy compounds and oximes to their corresponding amines, but the reduction of amides under these conditions, although previously reported, is not well documented in major works of organic chemistry. This procedure is specially useful for industry since it is safer, less expensive, requires less time and provides higher yields (65-80 per cent) when compared with lithium aluminium hydride or catalytic reduction methods.
The emphasized text is written in a slightly confusing language but nonetheless confirms that amides can be reduced to amines using $ceNa/ROH$, otherwise known as Bouveault-Blanc reduction.
References:
Bhandari, K. , Sharma, V. L. and Chatterjee, S. K. (1991), ChemInform Abstract: A Convenient Method for the Reduction of Amides to Their Corresponding Amines.. ChemInform, 22: no-no. DOI: 10.1002/chin.199118077
answered 1 hour ago
William R. EbenezerWilliam R. Ebenezer
1,243422
$endgroup$
Yes, that is used as a pathway for synthesis of amines from amides, albeit rarely.
I quote from the abstract of a communication that reports the same: (emphasis mine)
The reduction of amides to their corresponding amines has been used extensively in the synthesis of many drugs and their intermediates. This reaction has usually been carried out by means of metal hydrides (especially lithium aluminium hydride) or by catalytic hydrogenation over various catalysts. Metal and alcohol has been used for the reduction of ketones to their corresponding hydroxy compounds and oximes to their corresponding amines, but the reduction of amides under these conditions, although previously reported, is not well documented in major works of organic chemistry. This procedure is specially useful for industry since it is safer, less expensive, requires less time and provides higher yields (65-80 per cent) when compared with lithium aluminium hydride or catalytic reduction methods.
The emphasized text is written in a slightly confusing language but nonetheless confirms that amides can be reduced to amines using $ceNa/ROH$, otherwise known as Bouveault-Blanc reduction.
References:
Bhandari, K. , Sharma, V. L. and Chatterjee, S. K. (1991), ChemInform Abstract: A Convenient Method for the Reduction of Amides to Their Corresponding Amines.. ChemInform, 22: no-no. DOI: 10.1002/chin.199118077
answered 1 hour ago
William R. EbenezerWilliam R. Ebenezer
1,243422
answered 1 hour ago
William R. EbenezerWilliam R. Ebenezer
1,243422
answered 1 hour ago
William R. EbenezerWilliam R. Ebenezer
1,243422
answered 1 hour ago
William R. EbenezerWilliam R. Ebenezer
1,243422
1,243422
add a comment |
add a comment |
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