2-(2,6-Difluoro-phenyl)-6-nitro-benzo[d][1,3]oxazin-4-one → 6-Amino-2-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one

HRID 567680

Reaction equation

HRID 567680 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]2[N:8]=[C:9]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[F:20])[O:10][C:11](=[O:12])[C:6]=2[CH:5]=1)([O-])=O>C(O)(=O)C.O=[Pt]=O>[NH2:1][C:4]1[CH:22]=[CH:21][C:7]2[N:8]=[C:9]([C:13]3[C:14]([F:20])=[CH:15][CH:16]=[CH:17][C:18]=3[F:19])[O:10][C:11](=[O:12])[C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 212624642-(2,6-Difluoro-phenyl)-6-nitro-benzo[d][1,3]oxazin-4-one

Product 1

HCID 98603326-Amino-2-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

6-Nitro-2-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one (50 mg) was dissolved in acetic acid (5 mL) under N2, PtO2 (2.5 mg) was added and the mixture was hydrogenated with H2 gas. Reaction time 2 h. The reaction mixture was filtered through Hyflo®, which was rinsed afterwards with ethyl acetate. The combined organic phases were evaporated to dryness and subsequently treated three times with toluene followed by evaporation.

Workup

  1. customReaction time 2 h
  2. filtrationThe reaction mixture was filtered through Hyflo®, which
  3. washwas rinsed afterwards with ethyl acetate
  4. customThe combined organic phases were evaporated to dryness
  5. additionsubsequently treated three times with toluene
  6. customfollowed by evaporation

Sources & evidence

ORD record
ord-d8033a7ca60b434caf3c2f39c77958ee
Source dataset
uspto-grants-2001_01
Patent number
US06180625B2

Linked notes

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