Hydrogen Peroxide → 1-(2-benzoyloxyethyl)-1H-imidazo[4,5-c]-quinolin-5-oxide

HRID 255518Notes

Reaction equation

[C:1]([O:9][CH2:10][CH2:11][N:12]1[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:14]=[CH:13]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:25]O>C(O)(=O)C>[C:1]([O:9][CH2:10][CH2:11][N:12]1[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:17]([O-:25])=[CH:16][C:15]=2[N:14]=[CH:13]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 67.5 g (0.213 mole) of 1-(2-benzoyloxyethyl)-1H-imidazo[4,5-c]quinoline (from Example 118), 36.3 g (0.32 mole) of 30% hydrogen peroxide and 450 ml of glacial acetic acid was heated at 65° C. for two days with stirring. The solution was then evaporated in vacuo, and the residue was added to water. The mixture was neutralized with aqueous sodium hydroxide solution and sodium bicarbonate. The solid was separated by filtration, washed with water and recrystallized from methanol to provide tan solid 1-(2-benzoyloxyethyl)-1H-imidazo[4,5-c]-quinolin-5-oxide.

Workup

customThe solution was then evaporated in vacuo
additionthe residue was added to water
customThe solid was separated by filtration
washwashed with water
customrecrystallized from methanol

Sources & evidence

ORD record: ord-738837c7025047c8a2beea94bdc9239d
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04698348

Reaction notes

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