5-Methyl-2-nitroanisole → 2-Methoxy-p-toluidine

HRID 2170778Notes

Reaction equation

HRID 2170778 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-])=O)=[C:6]([O:8][CH3:9])[CH:7]=1>[Ni].CO.C1COCC1>[CH3:9][O:8][C:6]1[CH:7]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=1[NH2:10]

Participants

4

Reactant 1

HCID 974555-Methyl-2-nitroanisole

Product 1

HCID 1702192-Methoxy-p-toluidineYield 95.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 5-methyl-2-nitroanisole (2 g, 12 mmol) and Raney nickel (2.2 g) in MeOH/THF (120 mL, 3:1 v/v) was shaken for 20 h at RT and under 0.1 bar of H2. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated to afford 1.57 g of the title compound as colorless oil. HPLC: LtRet=1.44 min; LC-MS: m/z 138.1 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-91c9f892d9d148b7ac23e90d7259486a
Source dataset
uspto-grants-2015_06
Patent number
US09051279B2

Reaction notes

Loading…