2-Methyl-4-nitro-1-phenoxybenzene → 3-Methyl-4-phenoxyaniline

HRID 1781154Notes

Reaction equation

HRID 1781154 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:15]([O-])=O)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[NH2:15]

Participants

3

Reactant 1

HCID 186166912-Methyl-4-nitro-1-phenoxybenzene

Product 1

HCID 155504883-Methyl-4-phenoxyaniline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The nitro compound prepared above was reduced under H2 using 10% Pd/C catalyst in MeOH to give 3-methyl-4-phenoxyaniline. 1H NMR (CDCl3) δ 7.27 (m, 2H), 6.97 (m, 1H), 6.83 (m, 2H), 6.80 (d, 1H), 6.60 (d, 1H), 6.52 (m, 1H), 3.53 (br s, 2H), 2.11 (s, 3H). MS (DCl/NH3) m/e 200 (M+H)+, 217 (M+H+NH3)+.

Sources & evidence

ORD record
ord-bf5fec9254e74095aecd364f22ab9d66
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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