Ammonia → 8-nitro-2-(3-(trifluoromethyl)phenyl)quinazolin-4(3H)-one

HRID 520441Notes

Reaction equation

HRID 520441 reaction equation
[N+:1]([C:4]1[C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)[O:12][C:13](=O)[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH3:25].O>CC(O)C>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:9]=1[N:10]=[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1)[NH:25][C:13]2=[O:12])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 585528458-nitro-2-(3-(trifluoromethyl)phenyl)-4H-benzo[d][1,3]oxazin-4-one

Product 1

HCID 1361275808-nitro-2-(3-(trifluoromethyl)phenyl)quinazolin-4(3H)-oneYield 62%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

8-nitro-2-(3-(trifluoromethyl)phenyl)-4H-benzo[d][1,3]oxazin-4-one 3 (150 mg, 0.45 mmol) was added to a solution of ammonia (5.0 mL, 10 mmol) in IPA. The reaction mixture was heated under gentle reflux for 12 h then cooled to room temperature. The reaction mixture was poured into H2O and the resulting precipitate was collected by filtration rinsed with H2O and dried under vacuum. The crude residue was recrystallized from EtOAc to give 8 (91 mg, 62% yield) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder gentle reflux for 12 h
  3. filtrationthe resulting precipitate was collected by filtration
  4. washrinsed with H2O
  5. customdried under vacuum
  6. customThe crude residue was recrystallized from EtOAc

Sources & evidence

ORD record
ord-7702e6567cc94191a88bf393728d9aa6
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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