Hydrochloric Acid → HCID 86742616, compound

HRID 414343Notes

Reaction equation

HRID 414343 reaction equation
[C:1]([C:9]1[CH:20]=[C:19]([Cl:21])[C:12]2[O:13][CH:14]([C:16]([OH:18])=[O:17])[CH2:15][C:11]=2[C:10]=1[Cl:22])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:24][OH:25].Cl>N1C=CC=CC=1>[Cl:22][CH:10]1[C:11]2[C:12]([O:13][CH:14]([C:16]([OH:18])=[O:17])[CH:15]=2)=[C:19]([Cl:21])[CH:20]=[C:9]1[C:1](=[N:24][OH:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 143487715-Benzoyl-4,7-dichloro-2,3-dihydro-1-benzofuran-2-carboxylic acid

Product 1

HCID 86742616HCID 86742616, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5-benzoyl-4,7-dichloro-2,3-dihydrobenzo[b]furan-2-carboxylic acid (2.5 g), hydroxylamine hydrochloride (5.2 g) and pyridine (50 ml) was stirred for 18 hours at 90°-100° C. After cooling, the mixture was rendered acidic with HCl and subjected to extraction with ether. Ether was distilled off and the residual water was removed by azeotropic distillation with benzene, yielding 2.6 g of 4,7-dichloro-2,4-dihydro-5-(α-hydroxyiminobenzyl)benzo[b]furan-2-carboxylic acid. This compound (2.6 g) was dissolved in 20 ml of anhydrous dimethylformamide, and to the ice-cooled solution, 0.9 g of 60% sodium hydride was added in small portions under stirring. After continuing the agitation for 7 hours at room temperature, the mixture was left to stand overnight. After addition of 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 with acetonitrile-benzene, yielding 0.9 g of 5-chloro-7,8-dihydro-3-phenylfuro[2,3-g]-1,2-benzisoxazole-7-carboxylic acid. The physical data of this compound were in agreement with those of the product obtained in Example 3.

Workup

  1. temperatureAfter cooling
  2. extractionsubjected to extraction with ether
  3. distillationEther was distilled off
  4. customthe residual water was removed by azeotropic distillation with benzene

Sources & evidence

ORD record
ord-dd29a149e5184032847178553e90db53
Source dataset
uspto-grants-1988_12
Patent number
US04791209

Reaction notes

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