Hydroxyamine hydrochloride → HCID 86742619, compound

HRID 414352Notes

Reaction equation

HRID 414352 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[C:5]([C:7]1[CH:18]=[C:17]([Cl:19])[C:10]2[O:11][CH:12]([C:14]([OH:16])=[O:15])[CH2:13][C:9]=2[C:8]=1[Cl:20])=O.Cl.[NH2:25][OH:26]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[C:5]([C:7]1[CH:18]=[C:17]([Cl:19])[C:10]2[O:11][CH:12]([C:14]([OH:16])=[O:15])[CH2:13][C:9]=2[C:8]=1[Cl:20])=[N:25][OH:26]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 14348782HCID 14348782, compound

Product 1

HCID 86742619HCID 86742619, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5-(3-chlorobenzoyl)-4,7-dichloro-2,3-dihydrobenzo[b]furan-2-carboxylic acid (11.5 g), hydroxylamine hydrochloride (21.5 g) and pyridine (110 ml) was refluxed for 14 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 an.d dried. By distilling off the solvent, 12 g of 5-(3-chloro-α-hydroxyiminobenzyl)4,7-dichloro-2,3-dihydrobenzo[b]furan-2-carboxylic acid was obtained. This compound (12 g) was dissolved in anhydrous dimethylformamide (150 ml), and to the ice-cooled solution, 3.9 g of 60% sodium hydride was added in small amounts under agitation. After stirring for 8 hours at room temperature, the mixture was left to stand overnight. After adding water, the mixture 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 5.6 g of 5-chloro- 3-(3-chlorophenyl)-7,8-dihydrofuro[2,3-g]-1,2-benzisoxazole-7-carboxylic acid. m.p. 168°-169° C. This compound exhibited a mass spectrum having a molecular ion peak at m/e 349.

Workup

  1. temperaturewas refluxed for 14 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-f639f6d420a34fce9e8f28142bb0a46d
Source dataset
uspto-grants-1988_12
Patent number
US04791209

Reaction notes

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