Hydroxyamine hydrochloride → HCID 86742618, compound

HRID 414351Notes

Reaction equation

HRID 414351 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[CH:19]=[C:18]([Cl:20])[C:11]3[O:12][CH:13]([C:15]([OH:17])=[O:16])[CH2:14][C:10]=3[C:9]=2[Cl:21])=O)=[CH:4][CH:3]=1.Cl.[NH2:25][OH:26]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[CH:19]=[C:18]([Cl:20])[C:11]3[O:12][CH:13]([C:15]([OH:17])=[O:16])[CH2:14][C:10]=3[C:9]=2[Cl:21])=[N:25][OH:26])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 14348780HCID 14348780, compound

Product 1

HCID 86742618HCID 86742618, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5-(4-chlorobenzoyl)-4,7-dichloro-2,3-dihydrobenzo[b]furan-2-carboxylic acid (10.8 g), hydroxylamine hydrochloride (20.7 g) and pyridine (100 ml) was refluxed for 13 hours. After 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, 11.0 g of 5-(4-chloro-α-hydroxyiminobenzyl)4,7-dichloro-2,3-dihydrobenzo[b]furan-2-carboxylic acid was obtained. This compound (11 g) was dissolved in anhydrous dimethylformamide (140 ml), and to the ice-cooled solution, 4.0 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 6.5 g of 5-chloro-3-(4-chlorophenyl)-7,8-dihydrofuro[2,3-g]-1,2-benzisoxazole-7-carboxylic acid. m.p. 240°-243° C. (with decomposition). This compound exhibited a mass spectrum having a molecular ion peak at m/e 349.

Workup

  1. temperaturewas refluxed for 13 hours
  2. distillationAfter 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-9adbe26671f94f889e854eb459e69c08
Source dataset
uspto-grants-1988_12
Patent number
US04791209

Reaction notes

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