3-[4-(2-Chlorobenzyl)-indol-3-yl]-4-methoxy-2-nitrobutyric acid ethyl ester → 2-Amino-3-[4-(2-chlorobenzyl)-indol-3-yl]-4-methoxybutyric acid ethyl ester

HRID 1720321Notes

Reaction equation

HRID 1720321 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH:5]([N+:27]([O-])=O)[CH:6]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[NH:12][CH:11]=1)[CH2:7][O:8][CH3:9])[CH3:2]>C(O)C.[Ni]>[CH2:1]([O:3][C:4](=[O:30])[CH:5]([NH2:27])[CH:6]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[NH:12][CH:11]=1)[CH2:7][O:8][CH3:9])[CH3:2]

Participants

4

Reactant 1

HCID 544982583-[4-(2-Chlorobenzyl)-indol-3-yl]-4-methoxy-2-nitrobutyric acid ethyl ester

Product 1

HCID 537537032-Amino-3-[4-(2-chlorobenzyl)-indol-3-yl]-4-methoxybutyric acid ethyl esterYield 92.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

6.1 g (0.014 mol) of 3-[4-(2-chlorobenzyl)-indol-3-yl]-4-methoxy-2-nitrobutyric acid ethyl ester is hydrogenated in 125 ml of ethanol with 6 g of Raney nickel at standard pressure and room temperature. After 41/2 hours the hydrogen absorption is completed. The Raney nickel is filtered off, the filtrate is concentrated by evaporation and a crude product of 5.2 g of 2-amino-3-[4-(2-chlorobenzyl)-indol-3-yl]-4-methoxybutyric acid ethyl ester is obtained, that is used without further purification in the next stage.

Workup

  1. customAfter 41/2 hours the hydrogen absorption
  2. filtrationThe Raney nickel is filtered off
  3. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-f38774a7e8214b13afb2ccdd0acea0ff
Source dataset
uspto-grants-1996_04
Patent number
US05506234

Reaction notes

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