Pyridinium chloride → 3-(4-Chloro-phenyl)-benzo[D]isoxazol-6-OL

HRID 568720Notes

Reaction equation

HRID 568720 reaction equation
Cl.N1C=CC=CC=1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]3[CH:20]=[CH:21][C:22]([O:24]C)=[CH:23][C:18]=3[O:17][N:16]=2)=[CH:11][CH:10]=1>>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:19]3[CH:20]=[CH:21][C:22]([OH:24])=[CH:23][C:18]=3[O:17][N:16]=2)=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 140125163-(4-Chlorophenyl)-6-methoxy-1,2-benzisoxazole

Product 1

HCID 1355896553-(4-Chloro-phenyl)-benzo[D]isoxazol-6-OL

Conditions

Temperature
210 °C

Procedure

A mixture of 60 g of pyridine hydrochloride and 12.0 g 3-(4-chlorophenyl)-6-methoxy-1,2-benzisoxazole is heated with stirring at 210° C. for 75 min. The hot reaction mixture is poured with vigorous stirring onto ice and the solid is filtered, dried, and recrystallized from toluene to afford 3-(4-chlorophenyl)-6-hydroxy-1,2-benzisoxazole, mp 203° C.

Workup

  1. temperatureis heated
  2. additionThe hot reaction mixture is poured
  3. stirringwith vigorous stirring onto ice
  4. filtrationthe solid is filtered
  5. customdried
  6. customrecrystallized from toluene

Sources & evidence

ORD record
ord-3114b57039f7407c8e0d48534ceda64b
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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