2-(2,6-Difluoro-phenyl)-7-nitro-benzo[d][1,3]oxazin-4-one → 7-Amino-2-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one

HRID 567684Notes

Reaction equation

HRID 567684 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[O:13])[O:11][C:10]([C:14]3[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=3[F:21])=[N:9][C:8]=2[CH:22]=1)([O-])=O>C(O)(=O)C.O=[Pt]=O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[O:13])[O:11][C:10]([C:14]3[C:15]([F:21])=[CH:16][CH:17]=[CH:18][C:19]=3[F:20])=[N:9][C:8]=2[CH:22]=1

Participants

4

Reactant 1

HCID 104477332-(2,6-Difluoro-phenyl)-7-nitro-benzo[d][1,3]oxazin-4-one

Product 1

HCID 98819927-Amino-2-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

7-Nitro-2-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one (0.10 g) was dissolved in acetic acid (10 mL) under N2, PtO2 (5 mg) was added and the mixture was hydrogenated with H2 gas. Reaction time 1 day. 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 1 day
  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-1d1d3e34ba904e49bc320da92f48fc2d
Source dataset
uspto-grants-2001_01
Patent number
US06180625B2

Reaction notes

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