Methyl 3-methoxy-4-nitrobenzoate → Methyl 4-amino-3-methoxybenzoate

HRID 2246065Notes

Reaction equation

HRID 2246065 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[C:6]([O:13][CH3:14])[CH:5]=1>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([O:13][CH3:14])[CH:5]=1

Participants

4

Reactant 1

HCID 287308Methyl 3-methoxy-4-nitrobenzoate

Product 1

HCID 602411Methyl 4-amino-3-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A 2-L, Parr high-pressure hydrogenation bottle (glass rated to 80 psi) was charged with Pd/C (10 wt % on Carbon, 5 g), ethyl acetate (800 mL) and 32 (120.5 g, 0.57 mol). The reaction mixture was charged with H2 (30 psi) on a Parr apparatus. Charging H2 was continued carefully several times until the pressure remained steady. This took approximately about 3 h. The reaction was shaken for an additional 0.5 h. After the hydrogenation, the reaction mixture was diluted with ethyl acetate to dissolve some of the precipitated product and directly passed through a short pad of Celite, and washed with ethyl acetate. The solvent was evaporated to yield 4-amino-3-methoxy-benzoic acid methyl ester 33 as a white solid. 1H NMR (400 MHz, CDCl3) δ: 7.55 (dd, 1H), 7.45 (d, 1H), 6.66 (d, 1H), 4.21 (s, 2H), 3.90 (s, 3H), 3.86 (s, 3H). MS (ES) m/z 182.1 (MH)+.

Workup

  1. additionThe reaction mixture was charged with H2 (30 psi) on a Parr apparatus
  2. dissolutionto dissolve some of the precipitated product
  3. washwashed with ethyl acetate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4699e7a62ae9477eb6217c95a2e1c72a
Source dataset
uspto-grants-2010_03
Patent number
US07687494B2

Reaction notes

Loading…