2-Nitro-4-chloro-6-methylanisole → 5-Chloro-2-methoxy-3-methylaniline

HRID 1166228Notes

Reaction equation

HRID 1166228 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[O:12][CH3:13])([O-])=O>C(O)C.[Pt]>[NH2:1][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[O:12][CH3:13]

Participants

4

Reactant 1

HCID 229976382-Nitro-4-chloro-6-methylanisole

Product 1

HCID 229976575-Chloro-2-methoxy-3-methylanilineYield 90.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2-nitro-4-chloro-6-methylanisole (16 g) and 10% Pt(S)/C (1.6 g) in ethanol was hydrogenated at 50 psi for 3 hours. After filtration and concentration, purification by flash chromatography over silica gel (eluted with 10% ethyl acetate in hexanes) gave 12.3 g (90%) of 2-amino-4-chloro-6-methylanisole. 1H NMR (300 MHz, CDCl3) δ6.58 (d, J=2.4 Hz, 1 H), 6.53 (d, J=2.4 Hz, 1 H), 3.77 (s, 3 H), 2.22 (s, 3 H).

Workup

  1. filtrationAfter filtration and concentration, purification by flash chromatography over silica gel (eluted with 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a6bf4dbab8824843a91118885753762c
Source dataset
uspto-grants-2003_09
Patent number
US06613786B2

Reaction notes

Loading…