3-(Trifluoromethyl)aniline → 3-Phenylquinazolinone

HRID 511780

Reaction equation

HRID 511780 reaction equation
C[C:2]1[O:3][C:4](=O)[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.FC(F)(F)[C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18]>CCOC(C)=O.CCCCCC>[C:17]1([N:18]2[CH:4]=[C:5]3[C:6]([CH:8]=[CH:9][CH:10]=[CH:11]3)=[N:7][C:2]2=[O:3])[CH:19]=[CH:20][CH:21]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 68236Acetanthranil

Product 1

HCID 671201143-PhenylquinazolinoneYield 56%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-methyl-4H-Benzo[d][1,3]oxazin-4-one (12; 1.0 g, 6.2 mmol) and 3-trifluoromethylaniline (13, R═H, 0.77 mL, 6.2 mmol, 1.0 eq) were heated at 160° C. (oil bath) for 12 hours. The reaction was cooled to room temperature and the resulting solid was subjected to chromatography on silica gel with 20-50% EtOAc/hexane. Product-containing fractions were pooled and evaporated to yield 1.08 g mg (56%) of 14 as a yellow solid: 1H NMR (CDCl3): 8.27 (d, 1H), 7.29-7.28 (m, 7H), 2.25 (s, 3H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customevaporated

Sources & evidence

ORD record
ord-d6100ca886bf40598d6f2c73cd29f468
Source dataset
uspto-grants-2015_08
Patent number
US09101635B2

Linked notes

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