Water → N-(4-amino-2'-methyl-biphenyl-2-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide

HRID 1267516Notes

Reaction equation

HRID 1267516 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([C:13]([CH3:35])([CH3:34])[C:14]([N:16]([CH3:33])[C:17]2[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[CH:19][C:18]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.O>O1CCCC1.FC(F)(F)C(O)=O>[NH2:23][C:21]1[CH:20]=[CH:19][C:18]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])=[C:17]([N:16]([CH3:33])[C:14](=[O:15])[C:13]([C:5]2[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=[C:3]([C:2]([F:1])([F:36])[F:37])[CH:4]=2)([CH3:34])[CH3:35])[CH:22]=1

Participants

5

Reactant 2

HCID 962WaterHCID 185464982-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(2'-methyl-4-nitro-biphenyl-2-yl)-isobutyramide

Product 1

HCID 18546507N-(4-amino-2'-methyl-biphenyl-2-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramideYield 99.4%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 950 mg (1.81 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(2′-methyl-4-nitro-biphenyl-2-yl)-isobutyramide in 12 ml tetrahydrofuran and 3 ml water 608 mg (10.87 mmol) iron powder and 3 drops trifluoroacetic acid were added. After heating at 85° for 3 hrs., the reaction mixture was cooled to room temperature and evaporated. The residue was purified by chromatography (SiO2, hexane/ethyl acetate 1:4) to give 890 mg (99%) N-(4-amino-2′-methyl-biphenyl-2-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide as pale yellow crystals, MS (ISP): 495.2 (M+H)+.

Workup

  1. temperatureAfter heating at 85° for 3 hrs
  2. customevaporated
  3. customThe residue was purified by chromatography (SiO2, hexane/ethyl acetate 1:4)

Sources & evidence

ORD record
ord-039b7f6f010f43d899fbba649099f095
Source dataset
uspto-grants-2003_04
Patent number
US06552088B2

Reaction notes

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