Hydrochloric Acid → HCID 13015768, compound

HRID 568629Notes

Reaction equation

HRID 568629 reaction equation
[Cl:1][C:2]1[C:3]([O:18][CH2:19][C:20]([O:22]CC)=[O:21])=[CH:4][C:5]2[O:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[F:16])[C:6]=2[CH:17]=1.C(O)C.Cl>O>[Cl:1][C:2]1[C:3]([O:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:4][C:5]2[O:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[F:16])[C:6]=2[CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14012493HCID 14012493, compound

Product 1

HCID 13015768HCID 13015768, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl {[5-chloro-3-(2-fluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetate (14 g) sodium hydroxide (8 g), ethanol (500 ml) and water (300 ml) is refluxed for five hours, cooled in an ice bath and acidified with concentrated hydrochloric acid. The suspension is extracted with chloroform, the extract dried with saturated sodium chloride and the chloroform removed to give a solid, mp 214°-215° C. Recrystallization from a 3:2 mixture of acetonitrile-toluene gives {[5-chloro-3-(2-fluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetic acid.

Workup

  1. temperatureis refluxed for five hours
  2. temperaturecooled in an ice bath
  3. extractionThe suspension is extracted with chloroform
  4. dry with materialthe extract dried with saturated sodium chloride
  5. customthe chloroform removed
  6. customto give a solid, mp 214°-215° C
  7. customRecrystallization
  8. additionfrom a 3:2 mixture of acetonitrile-toluene

Sources & evidence

ORD record
ord-20645d43565f411f8ac7485ac7d22924
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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