6-Nitro-o-anisidine → 3-Methoxybenzene-1,2-diamine

HRID 899661Notes

Reaction equation

HRID 899661 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH3:12]>CO.[Pd]>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH3:12]

Participants

4

Reactant 1

HCID 854916-Nitro-o-anisidine

Product 1

HCID 1842683-Methoxybenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-amino-3-nitroanisole (465 mg, 2.94 mmol) in methanol (50 mL) was added palladium on carbon (10% Pd, 100 mg). The mixture was then placed under an atmosphere of hydrogen gas (1 atm) and was stirred for one hour. The mixture was then filtered through celite and concentrated to give 2,3-diaminoanisole as a yellow foam in a yield of 400 mg (98%). 1H NMR (CDCl3) δ 3.45 (br s, 4H(NH)), 3.84 (s, 3H), 6.40 (m, 2H), 6.67 (t, 1H, J=7.8 Hz)

Workup

  1. filtrationThe mixture was then filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-70d93375020e4d7ea3b9fd42f9292b81
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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