1-[2-(2-Methoxy-ethoxy)-1,1-dimethyl-ethyl]-4-nitro-benzene → 4-[2-(2-Methoxy-ethoxy)-1,1-dimethyl-ethyl]-phenylamine
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]([N+:16]([O-])=O)=[CH:12][CH:11]=1)([CH3:9])[CH3:8]>CO.[Ni]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)([CH3:9])[CH3:8]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A suspension of 1-[2-(2-methoxy-ethoxy)-1,1-dimethyl-ethyl]-4-nitro-benzene (8.1 g, 32 mmol) and Raney Ni (1 g) in MeOH (50 mL) was stirred under H2 (1 atm) at room temperature for 1 h. The catalyst was filtered off and the filtrate was concentrated to obtain 4-[2-(2-methoxy-ethoxy)-1,1-dimethyl-ethyl]-phenylamine (5.5 g, 77%).
Workup
- filtrationThe catalyst was filtered off
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-20013f6b42704346bf0c6d050204ea59
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08629162B2
Reaction notes
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