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

HRID 275787

Reaction equation

HRID 275787 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]>C(OCC)(=O)C.[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-diamineYield 101.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-3-nitroanisole (4.3 g) was hydrogenated in ethyl acetate (200 ml) using catalytic 10% palladium on charcoal under an atmosphere of hydrogen at ambient temperature. Once complete the reaction mixture was filtered through Celite and the filtrate evaporated in vacuo to afford the title compound as a brown liquid (3.60 g).

Workup

  1. customat ambient temperature
  2. filtrationwas filtered through Celite
  3. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-1931361c855c4e49b5bf142cad92b2bd
Source dataset
uspto-grants-2002_03
Patent number
US06353010B1

Linked notes

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