Water → 8-nitro-2-(3-(trifluoromethyl)phenyl)-4H-benzo[d][1,3]oxazin-4-one

HRID 520436Notes

Reaction equation

HRID 520436 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[NH2:14][C:15]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](O)=[O:18].O>N1C=CC=CC=1>[N+:24]([C:23]1[C:15]2[N:14]=[C:6]([C:5]3[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=3)[O:7][C:17](=[O:18])[C:16]=2[CH:20]=[CH:21][CH:22]=1)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 962WaterHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 2196332-Amino-3-nitrobenzoic acid

Product 1

HCID 585528458-nitro-2-(3-(trifluoromethyl)phenyl)-4H-benzo[d][1,3]oxazin-4-oneYield 54.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-(trifluoromethyl)benzoyl chloride 2 (4.5 mL, 30.2 mmol) was added to a suspension of 2-amino-3-nitrobenzoic acid 1 (5.0 g, 27.5 mmol) in pyridine (65 mL). The reaction mixture was stirred at room temperature for 12 h then poured into ice cooled H2O (300 mL). The resulting precipitate was collected by filtration, rinsed with H2O, and dried under vacuum to give 3 (5 g, 51% yield) as a yellow solid which was used without further purification.

Workup

  1. additionthen poured into ice
  2. filtrationThe resulting precipitate was collected by filtration
  3. washrinsed with H2O
  4. customdried under vacuum

Sources & evidence

ORD record
ord-d9cc5416c88d4659bce75138ee3a524c
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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