Hydrochloric Acid → HCID 13826776, compound

HRID 569471Notes

Reaction equation

HRID 569471 reaction equation
[OH:1][C:2]1[C:3]([OH:17])=[CH:4][C:5]2[O:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]=2[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH:25](Cl)[C:26]([O:28]C)=[O:27].Cl>CN(C)C=O.O>[C:10]1([C:7]2[C:6]3[CH:16]=[C:2]4[O:1][CH:25]([C:26]([OH:28])=[O:27])[O:17][C:3]4=[CH:4][C:5]=3[O:9][N:8]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8315Methyl dichloroacetateHCID 11430Potassium CarbonateHCID 135589616105679-42-3

Product 1

HCID 13826776HCID 13826776, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5,6-dihydroxy-3-phenyl-1,2-benzisoxazole (2.9 g), potassium carbonate (10.7 g) and methyl dichloroacetate (3.7 g) in 50 ml of N,N-dimethylformamide was stirred at 90°-100° C. for 2.5 hours. After cooling, water (50 ml) was added to the mixture followed by stirring it at 90°-100° C. for 40 minutes. After cooling and acidifying the mixture with hydrochloric acid, the mixture was extracted with ether. The ether layer was washed with water, dried and evaporated to remove the solvent. The residue was washed with methylene chloride, recrystallized from acetone/water to give 2.0 g of 3-phenyl-1,3-dioxolo[4,5-f]-1,2-benzisoxazole-6-carboxylic acid. m.p.: 202.5°-203.5° C.

Workup

  1. temperatureAfter cooling
  2. stirringby stirring it at 90°-100° C. for 40 minutes
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with ether
  5. washThe ether layer was washed with water
  6. customdried
  7. customevaporated
  8. customto remove the solvent
  9. washThe residue was washed with methylene chloride
  10. customrecrystallized from acetone/water

Sources & evidence

ORD record
ord-f1d6be5924114c9091a4085c812bb2be
Source dataset
uspto-grants-1988_03
Patent number
US04732906

Reaction notes

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