1-Chloro-4-methoxy-2-methyl-5-nitrobenzene → 5-Chloro-2-methoxy-4-methylaniline

HRID 1166232Notes

Reaction equation

HRID 1166232 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH3:10])=[C:4]([N+:11]([O-])=O)[CH:3]=1>[Pt]>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH3:10])=[C:4]([NH2:11])[CH:3]=1

Participants

3

Reactant 1

HCID 158645661-Chloro-4-methoxy-2-methyl-5-nitrobenzene

Product 1

HCID 229976285-Chloro-2-methoxy-4-methylaniline

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

4-Chloro-5-methyl-2-aminoanisole was prepared by the same method as described in Step 2 of Preparation 2c except using 4-chloro-5-methyl-2-nitroanisole (20 g) and 10%Pt(S)/C (2 g). Workup gave crude 4-chloro-5-methyl-2-aminoanisole, V (16 g, 94%) which was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ6.69 (s, 1 H), 6.60 (s, 1 H), 3.81 (s, 3 H), 2.25 (s, 3 H).

Workup

  1. custom4-Chloro-5-methyl-2-aminoanisole was prepared by the same method

Sources & evidence

ORD record
ord-3142cb015ec14706851ef1e26f6689b3
Source dataset
uspto-grants-2003_09
Patent number
US06613786B2

Reaction notes

Loading…