Acetic Acid → HCID 20207247, compound

HRID 542808Notes

Reaction equation

HRID 542808 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:12])[C:7](=[O:11])[NH:8]2)=[CH:4][C:3]=1[O:13][CH3:14].C(O)(=[O:17])C>C(OC(=O)C)(=O)C.O.[O-2].[O-2].[O-2].[Cr+6]>[Cl:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]2[C:6](=[O:12])[O:11][C:7](=[O:17])[NH:8][C:9]=2[CH:10]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 159155246-Chloro-5-methoxy-1H-indole-2,3-dione

Product 1

HCID 20207247HCID 20207247, compound

Reagents, catalysts & solvents 3

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

Procedure

Chromium trioxide (4.7 g) was added in small portions to a stirred suspension of 6-chloro-5-methoxyisatin (5.9 g) in glacial acetic acid (22 ml) and acetic anhydride (22 ml) at 80°. Some spontaneous ignition of the chromium trioxide was observed where this reagent became exposed to the air in the stirring vortex. The mixture was cooled and diluted with water (100 ml). The solid product was recrystallised from industrial methylated spirit to give the novel compound 7-chloro-6-methoxy-1H-3,1-benzoxazine-2,4-dione containing some unreacted starting material.

Workup

  1. temperatureThe mixture was cooled
  2. customThe solid product was recrystallised from industrial methylated spirit

Sources & evidence

ORD record
ord-ce2ae0eda4ec4ec0900b632b0cf09dff
Source dataset
uspto-grants-1987_04
Patent number
US04659718

Reaction notes

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