8-(2-Chlorophenylamino)-6,7-difluoro-4-methylbenzo[d][1,2]oxazin-1-one → 7-(2-Chlorophenylamino)-5,6-difluoro-3-methyl-2,3-dihydro-isoindol-1-one

HRID 1723685Notes

Reaction equation

HRID 1723685 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[C:18]2[C:17](=O)[O:16][N:15]=[C:14]([CH3:20])[C:13]=2[CH:12]=[C:11]([F:21])[C:10]=1[F:22]>CC(O)=O.[Zn]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[C:10]([F:22])=[C:11]([F:21])[CH:12]=[C:13]2[C:18]=1[C:17](=[O:16])[NH:15][CH:14]2[CH3:20]

Participants

4

Reactant 1

HCID 674037018-(2-Chlorophenylamino)-6,7-difluoro-4-methylbenzo[d][1,2]oxazin-1-one

Product 1

HCID 674048837-(2-Chlorophenylamino)-5,6-difluoro-3-methyl-2,3-dihydro-isoindol-1-oneYield 74%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture solution of 8-(2-chlorophenylamino)-6,7-difluoro-4-methyl-benzo[d][1,2]oxazin-1-one (26 mg, 0.079 mmol) and Zn (30 mg, 0.46 mmol) in AcOH (2 mL) was heated for 1 hour at 85° C. The reaction mixture was filtered and the solid was washed with additional AcOH. The filtrate was concentrated in vacuo, diluted with EtOAc, and washed with saturated aqueous NaHCO3 and water. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to give the desired product (18 mg, 74%) that was used directly without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed with additional AcOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. additiondiluted with EtOAc
  5. washwashed with saturated aqueous NaHCO3 and water
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a59485d1cca4a4c8453ac53fab457e9
Source dataset
uspto-grants-2009_02
Patent number
US07485643B2

Reaction notes

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