4-amino-3-nitro-N-(6-trifluoromethylpyridin-3-yl)-benzamide → 3,4-diamino-N-(6-trifluoromethylpyridin-3-yl)-benzamide

HRID 1515052Notes

Reaction equation

HRID 1515052 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=2)=[O:7])=[CH:4][C:3]=1[N+:21]([O-])=O>C1COCC1.[Pt]>[NH2:21][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:2]=1[NH2:1])[C:6]([NH:8][C:9]1[CH:10]=[N:11][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:14]=1)=[O:7]

Participants

4

Reactant 1

HCID 669662254-amino-3-nitro-N-(6-trifluoromethylpyridin-3-yl)-benzamide

Product 1

HCID 669656813,4-diamino-N-(6-trifluoromethylpyridin-3-yl)-benzamide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4-amino-3-nitro-N-(6-trifluoromethylpyridin-3-yl)-benzamide (500 mg, 1.53 mmol) in THF (20 mL) was hydrogenated at one atm over Pt/C (50 mg) for 3 hours. The catalyst was filtered through Celite and washed with THF. The solvent was removed under reduced pressure to give 3,4-diamino-N-(6-trifluoromethylpyridin-3-yl)-benzamide as a yellow solid.

Workup

  1. filtrationThe catalyst was filtered through Celite
  2. washwashed with THF
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4056b359be5f40d7994d8945c7409051
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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