2,6-Dichloro-4-nitroanisole → 3,5-Dichloro-2-methoxyaniline

HRID 1166230Notes

Reaction equation

HRID 1166230 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([Cl:11])[C:5]=1[O:12][CH3:13])([O-])=O>[Pt]>[NH2:1][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([Cl:11])[C:5]=1[O:12][CH3:13]

Participants

3

Reactant 1

HCID 1698622,6-Dichloro-4-nitroanisole

Product 1

HCID 112177473,5-Dichloro-2-methoxyanilineYield 95.5%

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

2-Amino-4,6-dichloroanisole was prepared by same method as described in Step 2 of Preparation 2c except using 2-nitro-4,6-dichloroanisole (13.32 g) and 10%Pt(S)/C (1.33 g). Workup gave crude 2-amino-4,6-dichloroanisole (11 g, 95%) which was used in the next step without purification. 1H NMR (300 MHz, CDCl3) δ6.73 (d, J=2.4 Hz, 1 H), 6.62 (d, J=2.4 Hz, 1 H), 3.82 (s, 3 H).

Workup

  1. custom2-Amino-4,6-dichloroanisole was prepared by same method

Sources & evidence

ORD record
ord-2ef161a605444e929cf327adb37597dc
Source dataset
uspto-grants-2003_09
Patent number
US06613786B2

Reaction notes

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