HCID 57567342, compound → HCID 57567410, compound

HRID 1915344Notes

Reaction equation

HRID 1915344 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][C:11]=1[N+:20]([O-])=O)([CH3:9])[CH3:8]>CO.[Ni]>[NH2:20][C:11]1[CH:12]=[C:13]([NH:16][C:17](=[O:19])[CH3:18])[CH:14]=[CH:15][C:10]=1[C:7]([CH3:9])([CH3:8])[CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1]

Participants

4

Reactant 1

HCID 57567342HCID 57567342, compound

Product 1

HCID 57567410HCID 57567410, compoundYield 35.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-{4-[2-(2-methoxy-ethoxy)-1,1-dimethyl-ethyl]-3-nitro-phenyl}-acetamide (5 g, 16 mmol) and Raney Ni (1 g) in MeOH (50 mL) was stirred under H2 (1 atm) at room temperature 1 h. The catalyst was filtered off and the filtrate was concentrated. The residue was purified by column chromatography (petroleum ether-EtOAc, 100:1) to give N-{3-amino-4-[2-(2-methoxy-ethoxy)-1,1-dimethyl-ethyl]-phenyl}-acetamide (1.6 g, 35%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography (petroleum ether-EtOAc, 100:1)

Sources & evidence

ORD record
ord-b1cfbed71809452aa76962f2d392434f
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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