4-Fluoro-3-(trifluoromethyl)aniline → HCID 178522141, compound

HRID 2185195Notes

Reaction equation

HRID 2185195 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[C:13]([N+:23]([O-:25])=[O:24])[CH:14]=[C:15]3[C:20]=2[N:19]=[C:18](Cl)[N:17]=[C:16]3[OH:22])=[O:10])=[CH:4][CH:3]=1.[F:26][C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][C:28]=1[C:34]([F:37])([F:36])[F:35]>CN1CCCC1=O.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[C:13]([N+:23]([O-:25])=[O:24])[CH:14]=[C:15]3[C:20]=2[N:19]=[C:18]([NH:31][C:30]2[CH:32]=[CH:33][C:27]([F:26])=[C:28]([C:34]([F:37])([F:35])[F:36])[CH:29]=2)[N:17]=[C:16]3[OH:22])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 753774-Fluoro-3-(trifluoromethyl)anilineHCID 178522140HCID 178522140, compound

Product 1

HCID 178522141HCID 178522141, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of N-(4-fluorophenyl)-2-chloro-4-hydroxy-6-nitroquinazoline-8-carboxamide (0.050 g) in 1-methyl-2-pyrrolidinone (1 mL) was added 4-fluoro-3-(trifluoromethyl)aniline (0.053 mL). The reaction mixture was heated at 130° C. for 4.5 h, then cooled to room temperature and diluted with water. The resulting mixture was cooled at 5° C. for 3 h and the precipitate which formed was isolated by filtration, washed with water and dried to afford the title compound as a grey solid (0.054 g). 1H NMR (300 MHz, DMSO-d6): 12.31 (s, 1H), 11.87 (s, 1H), 9.64 (s, 1H), 9.00 (d, J=2.9 Hz, 1H), 8.8. (d, J=2.9 Hz, 1H), 7.95-7.87 (m, 2H), 7.39-7.32 (m, 1H), 7.15-6.95 (m, 4H); HPLC (Method E): 4.3 min.; MS (APCI−): m/z 504.

Workup

  1. temperaturecooled to room temperature
  2. temperatureThe resulting mixture was cooled at 5° C. for 3 h
  3. customthe precipitate which formed
  4. customwas isolated by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-b72846803af74fb7911107a505a01e07
Source dataset
uspto-grants-2002_06
Patent number
US06399603B1

Reaction notes

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