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

HRID 1357375Notes

Reaction equation

HRID 1357375 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]>[Pd].C(Cl)Cl>[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-aminophthalate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

Palladium on activated charcoal (10% Pd, 200 mg) was added to a solution of 4-nitrophthalic acid dimethyl ester (2.0 g, 8.37 mmol) in methylene chloride (100 ml). The mixture was hydrogenated in a Parr apparatus at 207 kPa (30 psi) for 1½ hour. The mixture was filtered and evaporated to dryness in vacuo to give 4-aminophthalic acid dimethyl ester as white crystals (yield: 1.75 g (100%)). Mp: 83-85° C. 1H—NMR (CDCl3) in ppm: δ 3.80 (3H,s); 3.87 (3H,s); 6.6-6.7 (2H,m); 7.68 (1H,d).

Workup

  1. waitThe mixture was hydrogenated in a Parr apparatus at 207 kPa (30 psi) for 1½ hour
  2. filtrationThe mixture was filtered
  3. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-8354b0df5310469d8453b824adc810a5
Source dataset
uspto-grants-2003_07
Patent number
US06590118B1

Reaction notes

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