Hydrochloric Acid → 5-carbamoylspiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one

HRID 894638Notes

Reaction equation

[C:1]([C:3]1[CH:14]=[CH:13][C:6]2[O:7][C:8]3([C:11](=[O:12])[C:5]=2[CH:4]=1)[CH2:10][CH2:9]3)#[N:2].[OH:15]O.[OH-].[Na+].Cl>C(O)C>[C:1]([C:3]1[CH:14]=[CH:13][C:6]2[O:7][C:8]3([C:11](=[O:12])[C:5]=2[CH:4]=1)[CH2:10][CH2:9]3)(=[O:15])[NH2:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5-cyanospiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one (185 mg.) in ethanol (10 ml.) were added dropwise 5.5 ml. of 7% aqueous solution of hydrogen peroxide and 3.7 ml. of ethanol, then, to the mixture, was added 2 N aqueous solution of sodium hydroxide to adjust pH 10 and the solution was stirred at 60° C. for 2 hours. After cooling, the reaction mixture was neutralized with diluted hydrochloric acid and diluted with ice-water. The preciptating crystals were collected by filtration, washed with water and recrystallized from ethanol to give colorless needles of 5-carbamoylspiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one (106 mg.). m.p. 243°-244° C.

Workup

temperatureAfter cooling
filtrationThe preciptating crystals were collected by filtration
washwashed with water
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-5f8c4c8653d048968f27713f5bde8c1f
Source dataset: uspto-grants-1981_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04284644

Reaction notes

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