Nitric Acid → HCID 14012519, compound

HRID 568695Notes

Reaction equation

HRID 568695 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:18][CH2:19][C:20]([OH:22])=[O:21].[N+:23]([O-])([OH:25])=[O:24]>>[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([C:11]3[CH:16]=[C:15]([N+:23]([O-:25])=[O:24])[CH:14]=[CH:13][C:12]=3[F:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:18][CH2:19][C:20]([OH:22])=[O:21]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 194453((7-Chloro-3-(2-fluorophenyl)-1,2-benzisoxazol-6-yl)oxy)acetic acid

Product 1

HCID 14012519HCID 14012519, compound

Procedure

To a solution of 10.0 g of {[7-chloro-3-(2-fluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetic acid in 70 ml of ice-cold sulfuric acid, 2.5 ml of 16N nitric acid is added. The reaction mixture is stirred for 2 hr in the cold and then allowed to warm to room temperature over 1 hr. The reaction mixture is then poured onto ice and the solid is collected. The filter cake is washed with water until the washes are no longer acidic and then recrystallized from acetic acid to afford {[7-Chloro-3-(2-fluoro-5-nitrophenyl)-1,2-benzisoxazol-6-yl]oxy}acetic acid, mp 238°-240° C.

Workup

  1. additionThe reaction mixture is then poured onto ice
  2. customthe solid is collected
  3. washThe filter cake is washed with water until the washes
  4. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-aefe585cbd61445e8b3308ac5fbd6245
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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