Ethanol → 4-Amino-2-Ethyl-alpha-oxo-1-(phenylmethyl)-1H-indole-3-Acetamide

HRID 3387Notes

Reaction equation

HRID 3387 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:5]2[C:10]([C:11]=1[C:12](=[O:16])[C:13]([NH2:15])=[O:14])=[C:9]([N+:17]([O-])=O)[CH:8]=[CH:7][CH:6]=2)[CH3:2].CCO>C1COCC1>[NH2:17][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[C:11]([C:12](=[O:16])[C:13]([NH2:15])=[O:14])=[C:3]([CH2:1][CH3:2])[N:4]2[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 106416582-(1-Benzyl-2-ethyl-4-nitro-1H-indol-3-yl)-2-oxo-acetamide

Product 1

HCID 107581224-Amino-2-Ethyl-alpha-oxo-1-(phenylmethyl)-1H-indole-3-AcetamideYield 30.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.0 g (17.1 mmol) of 2-Ethyl-4-Nitro-α-oxo-1-(phenylmethyl)-1H-indole-3-acetamide in 140 ml of 1:1 THF:EtOH containing 1,0 g of 5% Pt/BaSO4 was hydrogenated at room temperature and 60 psi (4.22 Kg/cm2) for four hours. The catalyst was filtered and the filtrate evaporated in vacuo. The residue was chromatographed over silica gel eluting with Hexane/50 to 100% EtOAC to give 1.66 g (30%) of 4-Amino-2-Ethyl-α-oxo-1-(phenylmethyl)-1H-indole-3-Acetamide melting at 140°-144° C.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered
  3. customthe filtrate evaporated in vacuo
  4. customThe residue was chromatographed over silica gel eluting with Hexane/50 to 100% EtOAC

Sources & evidence

ORD record
ord-530aa127a76e4169b9ca650bd1dc8905
Source dataset
uspto-grants-1998_03
Patent number
US05733923

Reaction notes

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