1,2-Benzenedicarboxylic acid, 4-nitro-, 1,2-dimethyl ester → Dimethyl 4-aminophthalate

HRID 331534

Reaction equation

HRID 331534 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:5](=[CH:10][C:11]([N+:14]([O-])=O)=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:5](=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 691191,2-Benzenedicarboxylic acid, 4-nitro-, 1,2-dimethyl ester

Product 1

HCID 95886Dimethyl 4-aminophthalateYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of dimethyl-4-nitrophthalate (15.0 g, 62.7 mmol) and 10% Pd—C (1.5 g) in ethyl acetate (100 mL) was hydrogenated at 50 psi overnight. The reaction mixture was filtered through Celite, and the filter was washed with additional ethyl acetate (50 mL). The solvent was evaporated, and the residue was stirred in hexanes. The solid was filtered, washed with additional hexanes and dried to give 12.77 g of 4-amino-phthalic acid dimethyl ester as a pale orange solid, in 97% yield; 1H NMR (DMSO-d6) δ 3.71 (s, 3H), 3.75 (s, 3H), 6.17 (s, 2H), 6.58-6.65 (m, 2H), 7.57 (d, J=8.4 Hz, 1H).

Workup

  1. customwas hydrogenated at 50 psi overnight
  2. filtrationThe reaction mixture was filtered through Celite
  3. washthe filter was washed with additional ethyl acetate (50 mL)
  4. customThe solvent was evaporated
  5. filtrationThe solid was filtered
  6. washwashed with additional hexanes
  7. customdried

Sources & evidence

ORD record
ord-c16904127f5d46fca52e3e34f3fc0e50
Source dataset
uspto-grants-2014_11
Patent number
US08877780B2

Linked notes

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