Hydroxyamine hydrochloride → HCID 86742617, compound

HRID 414350Notes

Reaction equation

HRID 414350 reaction equation
[Cl:1][C:2]1[C:10]2[CH2:9][CH:8]([C:11]([OH:13])=[O:12])[O:7][C:6]=2[C:5]([Cl:14])=[CH:4][C:3]=1[C:15](=O)[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1.Cl.[NH2:25][OH:26]>N1C=CC=CC=1>[Cl:1][C:2]1[C:10]2[CH2:9][CH:8]([C:11]([OH:13])=[O:12])[O:7][C:6]=2[C:5]([Cl:14])=[CH:4][C:3]=1[C:15](=[N:25][OH:26])[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 14348776HCID 14348776, compound

Product 1

HCID 86742617HCID 86742617, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4,7-dichloro-2,3-dihydro-5-(4-fluorobenzoyl)benzo[b]furan-2-carboxylic acid (12.4 g), hydroxylamine hydrochloride (20.6 g) and pyridine (120 ml) was refluxed for 5.5 hours. Aftre distilling off the solvent, water was added to the mixture, which then was rendered acidic with HCl and subjected to extraction with ether. The ether layer was washed with water and dried. By distilling off the solvent, 12.8 g of 4,7-dichloro-2,3-dihydro-5-(4-fluoro-α-hydroxyiminobenzyl)benzo[b]furan-2-carboxylic acid was obtained. This compound (12.8 g) was dissolved in 150 ml of anhydrous dimethylformamide, and to the ice-cooled solution, 4.8 g of 60% sodium hydride was added in small portions under agitation. After continuing the agitation for 5 hours at room temperature, the mixture was left to stand overnight. Water was added to the mixture, which then was rendered acidic with HCl and subjected to extraction with ether. The ether layer was washed with water and dried. After distilling off the solvent, the residue was recrystallized from acetone-water, yielding 4.4 g of 5-chloro-7,8-dihydro-3-(4-fluorophenyl)furo[2,3-g]-1,2-benzisoxazole-7-carboxylic acid. m.p. 215°-218° C. This compound exhibited a mass spectrum having a molecular ion peak at m/e 333.

Workup

  1. temperaturewas refluxed for 5.5 hours
  2. distillationAftre distilling off the solvent, water
  3. additionwas added to the mixture, which
  4. extractionsubjected to extraction with ether
  5. washThe ether layer was washed with water
  6. customdried
  7. distillationBy distilling off the solvent

Sources & evidence

ORD record
ord-72a7207a3ae642ffbd62177aa4c82f1c
Source dataset
uspto-grants-1988_12
Patent number
US04791209

Reaction notes

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