Acetic Acid → 5,7-dichloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

HRID 1449551Notes

Reaction equation

HRID 1449551 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[C:4](=[O:13])[C:5](=[O:12])[NH:6]2.C(O)(=[O:16])C>C(OC(=O)C)(=O)C.O.[O-2].[O-2].[O-2].[Cr+6]>[Cl:1][C:2]1[C:3]2[C:4](=[O:13])[O:12][C:5](=[O:16])[NH:6][C:7]=2[CH:8]=[C:9]([Cl:11])[CH:10]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 2519084,6-Dichloroisatin

Product 1

HCID 123632155,7-dichloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dioneYield 72%

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalyst2×HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Procedure

To a stirred solution of 4,6-dichloro-1H-indole-2,3-dione (5.00 g, 23.2 mM) in acetic acid (21 mL) and acetic anhydride (21 mL) at 80° C. was added in small portions chromium trioxide (4.12 g, 41.3 mM). The temperature of the reaction mixture was maintained between 80°-90° C. during the addition of the chromium trioxide. After the addition was complete, the reaction mixture was diluted with water (100 mL) and then filtered to separate the precipitated solids. The solids were washed thoroughly with water and then dried to obtain the title compound as a yellow solid (4.13 g, 72%); MS(CI): 232 (M+H).

Workup

  1. additionAfter the addition
  2. filtrationfiltered
  3. customto separate the precipitated solids
  4. washThe solids were washed thoroughly with water
  5. customdried

Sources & evidence

ORD record
ord-919f4032293e49f588572defb34f149b
Source dataset
uspto-grants-1997_02
Patent number
US05599814

Reaction notes

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