Nitric Acid → HCID 14012519, compound

HRID 652925Notes

Reaction equation

HRID 652925 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 10.9 g of {[7-chloro-3-(2-fluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetic acid in 70 ml of ice-cold sulfuric acid, 2.2 ml of 16N nitric acid is added. The reaction mixture is stirred in the cold for 2 hr, allowed to warm to room temperature over 1 hr and poured into ice-water. The precipitate is collected to afford {[7-chloro-3-(2-fluoro-5-nitrophenyl)-1,2-benzisoxazol-6-yl]oxy}acetic acid. The fluoro-compound is treated with excess sodium methoxide in refluxing methanol for a total of 48 hr. The reaction mixture is acidified and the product is collected by filtration. Recrystallization from acetonitrile affords {[7-Chloro-3-(2-methoxy-5-nitrophenyl)-1,2-benzisoxazol-6-yl]oxy}acetic acid, mp 260°-262° C. (dec.)

Workup

  1. customThe precipitate is collected

Sources & evidence

ORD record
ord-b37e135171a446b8942cd3078608380b
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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