Hi All,
I haven't seen this elsewhere so I figured I'd post it. I'd upload the paper, but unfortunately when I try to do so it puts my personal info all over the pdf. I'll provide the paper info, procedure, and pertinent substrates
Magnesium?Catalyzed Proficient Reduction of Oximes to Amines Using Ammonium Formate
K. Abiraj & D. Channe Gowda
SYNTHETIC COMMUNICATIONSw Vol. 34, No. 4, pp. 599–605, 2004
DOI: 10.1081/SCC-120027707
Abstract:
Various aldoximes and ketoximes were selectively reduced to the corresponding amines by catalytic transfer hydrogenation employing low cost magnesium powder and ammonium formate at room temperature. Many other functionalities such as halogens, – OH, – OCH3, – COOH and –CH3 remained unaffected. The hydrogenation is fast, mild, clean, cost effective and high yielding.
Procedure:
Magnesium powder is washed with 0.01 N HCl for approximately two minutes, then filtered and washed with water, then dry methanol.
Typical Procedure
To a solution of the substrate (10mmol) in methanol or in any other suitable solvent (20mmol) was added ammonium formate (30mmol) and magnesium powder (1 g, 0.041 mol). The mixture was stirred under nitrogen atmosphere at room temperature. The reaction was exothermic and effervescent. After the completion of reaction (monitored by TLC), the reaction mixture was filtered through celite. The organic layer is evaporated and the residue was dissolved in chloroform or dichloromethane or ether and washed with saturated sodium chloride solution to remove excess ammonium formate. The organic layer was dried over anhydrous sodium sulphate and evaporation of the organic layer followed by purification either by preparative TLC or by column chromatography to yield the desired product.
p-OH-phenylacetone oxime to para-OH-amphetamine: 92% yield after 52 minute reaction
I haven't seen this elsewhere so I figured I'd post it. I'd upload the paper, but unfortunately when I try to do so it puts my personal info all over the pdf. I'll provide the paper info, procedure, and pertinent substrates
Magnesium?Catalyzed Proficient Reduction of Oximes to Amines Using Ammonium Formate
K. Abiraj & D. Channe Gowda
SYNTHETIC COMMUNICATIONSw Vol. 34, No. 4, pp. 599–605, 2004
DOI: 10.1081/SCC-120027707
Abstract:
Various aldoximes and ketoximes were selectively reduced to the corresponding amines by catalytic transfer hydrogenation employing low cost magnesium powder and ammonium formate at room temperature. Many other functionalities such as halogens, – OH, – OCH3, – COOH and –CH3 remained unaffected. The hydrogenation is fast, mild, clean, cost effective and high yielding.
Procedure:
Magnesium powder is washed with 0.01 N HCl for approximately two minutes, then filtered and washed with water, then dry methanol.
Typical Procedure
To a solution of the substrate (10mmol) in methanol or in any other suitable solvent (20mmol) was added ammonium formate (30mmol) and magnesium powder (1 g, 0.041 mol). The mixture was stirred under nitrogen atmosphere at room temperature. The reaction was exothermic and effervescent. After the completion of reaction (monitored by TLC), the reaction mixture was filtered through celite. The organic layer is evaporated and the residue was dissolved in chloroform or dichloromethane or ether and washed with saturated sodium chloride solution to remove excess ammonium formate. The organic layer was dried over anhydrous sodium sulphate and evaporation of the organic layer followed by purification either by preparative TLC or by column chromatography to yield the desired product.
p-OH-phenylacetone oxime to para-OH-amphetamine: 92% yield after 52 minute reaction
Magnesium?Catalyzed Proficient Reduction of Oximes to Amines Using Ammonium Formate.pdf
