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

HRID 127572Notes

Reaction equation

HRID 127572 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]>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

4

Reactant 1

HCID 53708925N-(2-chloro-6-nitrobenzyl)-L-alanine ethyl ester

Product 1

HCID 54486256N-(2-amino-6-chlorobenzyl)-L-alanine ethyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 14.3 g of N-(2-chloro-6-nitrobenzyl)-L-alanine ethyl ester in 50 ml of absolute ethanol was hydrogenated in the presence of 1 g of Raney nickel. After completion of the hydrogenation, the catalyst was filtered off and the filtrate was evaporated to dryness. There were obtained 12.6 g (99% of theory) of N-(2-amino-6-chlorobenzyl)-L-alanine ethyl ester; nD22 =1.5430.

Workup

  1. filtrationAfter completion of the hydrogenation, the catalyst was filtered off
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-dabc0e0b0de24a699e6448bf16b48244
Source dataset
uspto-grants-1981_03
Patent number
US04256748

Reaction notes

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