2-(3,5-Bis-trifluoromethyl-benzoylamino)-4-nitro-benzoic acid methyl ester → 4-Amino-2-(3,5-bis-trifluoromethyl-benzoylamino)-benzoic acid methyl ester

HRID 29668Notes

Reaction equation

HRID 29668 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[NH:13][C:14](=[O:29])[C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=1>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[NH:13][C:14](=[O:29])[C:15]1[CH:16]=[C:17]([C:25]([F:27])([F:28])[F:26])[CH:18]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:20]=1

Participants

4

Reactant 1

HCID 865973982-(3,5-Bis-trifluoromethyl-benzoylamino)-4-nitro-benzoic acid methyl ester

Product 1

HCID 865973994-Amino-2-(3,5-bis-trifluoromethyl-benzoylamino)-benzoic acid methyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(3,5-bis-trifluoromethyl-benzoylamino)-4-nitro-benzoic acid methyl ester (1.85 g, 4.24 mmol) in ethyl acetate (250 mL) in a Parr flask was added 10% palladium on carbon (0.20 g). The flask was attached to a Parr shaker and purged with nitrogen gas. The flask was then charged to 50 psi with hydrogen gas and the shaker was activated. After 2 hours the apparatus was recharged to 50 psi with hydrogen gas and the mixture was allowed to agitate. After an additional 2 hours the apparatus was recharged to 50 psi with hydrogen gas and the mixture was allowed to agitate for 4 additional hours (8 hours total time). The mixture was removed from the apparatus and filtered through a plug of Celite. The Celite was rinsed with ethyl acetate until no more color came through and the filtrate was concentrated under reduced pressure. The crude material was dissolved in ethyl acetate, dried over MgSO4, filtered and concentrated under reduced pressure to give 4-amino-2-(3,5-bis-trifluoromethyl-benzoylamino)-benzoic acid methyl ester (1.70 g, 99%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6); δ 13.52 (s, 1H), 8.49 (s, 2H), 8.44 (s, 1H), 7.83 (d, 1H), 7.73 (d, 1H), 6.40-6.36 (m, 2H), 6.37 (s, 2H), 6.36 (dd, 1H), 3.80 (s, 3H).

Workup

  1. custompurged with nitrogen gas
  2. additionThe flask was then charged to 50 psi with hydrogen gas
  3. waitAfter an additional 2 hours the apparatus was recharged to 50 psi with hydrogen gas
  4. stirringto agitate for 4 additional hours (8 hours total time)
  5. customThe mixture was removed from the apparatus
  6. filtrationfiltered through a plug of Celite
  7. washThe Celite was rinsed with ethyl acetate until no more color
  8. concentrationwas concentrated under reduced pressure
  9. dissolutionThe crude material was dissolved in ethyl acetate
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d86618ab97074c04b898f65dd5244177
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Reaction notes

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