N-(2-chloro-6-nitrobenzyl)-D-alanine ethyl ester → N-(2-amino-6-chlorobenzyl)-D-alanine ethyl ester

HRID 127574Notes

Reaction equation

HRID 127574 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C@@H:5]([CH3:18])[NH:6][CH2:7][C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:17])[CH3:2].[H][H]>C(O)C.[Ni]>[CH2:1]([O:3][C:4](=[O:19])[C@@H:5]([CH3:18])[NH:6][CH2:7][C:8]1[C:9]([Cl:17])=[CH:10][CH:11]=[CH:12][C:13]=1[NH2:14])[CH3:2]

Participants

5

Reactant 2

HCID 53708924N-(2-chloro-6-nitrobenzyl)-D-alanine ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 54486255N-(2-amino-6-chlorobenzyl)-D-alanine ethyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 14.3 g of N-(2-chloro-6-nitrobenzyl)-D-alanine ethyl ester in 50 ml of ethanol was hydrogenated in the presence of 1 g of Raney nickel. 3.35 liters of hydrogen were taken up in 2 hours. The catalyst was then filtered off and the filtrate was evaporated to dryness. There were obtained 12.6 g (99% of theory) of N-(2-amino-6-chlorobenzyl)-D-alanine ethyl ester; nD23 =1.5405; [α]D =+55.8° (c=1% in ethanol).

Workup

  1. filtrationThe catalyst was then filtered off
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-aff6cb749c0b4b578c93a3c78a4729ed
Source dataset
uspto-grants-1981_03
Patent number
US04256748

Reaction notes

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