HCID 21262481, compound → HCID 21262469, compound

HRID 567682Notes

Reaction equation

HRID 567682 reaction equation
[N+:1]([C:4]1[C:13]2[C:12](=[O:14])[O:11][C:10]([C:15]3[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=3[F:22])=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.O=[Pt]=O>[NH2:1][C:4]1[C:13]2[C:12](=[O:14])[O:11][C:10]([C:15]3[C:16]([F:22])=[CH:17][CH:18]=[CH:19][C:20]=3[F:21])=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 21262481HCID 21262481, compound

Product 1

HCID 21262469HCID 21262469, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

5-Nitro-2-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one (0.4 g) was dissolved in acetic acid (30 mL) under N2, PtO2 (20 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. The resulting mixture was dissolved in THF and precipitated with hexane giving a crude product which was purified on a silicagel column using dichloromethane as eluent. One fraction was collected (51 mg), identified as 5-amino-2-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one, LC-MS 275 M+1, ELS purity 100%, mp. 197 C.

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
  7. dissolutionThe resulting mixture was dissolved in THF
  8. customprecipitated with hexane giving a crude product which
  9. customwas purified on a silicagel column
  10. customOne fraction was collected (51 mg)

Sources & evidence

ORD record
ord-faad810492db4f28b4052db3957386fd
Source dataset
uspto-grants-2001_01
Patent number
US06180625B2

Reaction notes

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