Ammonia → 4-chloro-1-(2-hydroxyethyl)-1H-imidazo[4,5-c]quinoline

HRID 1789419Notes

Reaction equation

C([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]=[C:16]([Cl:25])[C:15]=2[N:14]=[CH:13]1)(=O)C1C=CC=CC=1.N>CO>[Cl:25][C:16]1[C:15]2[N:14]=[CH:13][N:12]([CH2:11][CH2:10][OH:9])[C:24]=2[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:17]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 25.3 g (0.072 mole) of 1-(2-benzoyloxyethyl)-4-chloro-1H-imidazo[4,5-c]quinoline (from Example 117) and 500 ml of 10% ammonia in methanol was stirred at about 20° C. for three days, and was then filtered and finally evaporated to low volume. The slurry was mixed with diethyl ether, and the solid was separated by filtration, washed with ether and recrystallized from methanol to provide white crystals of 4-chloro-1-(2-hydroxyethyl)-1H-imidazo[4,5-c]quinoline, m.p. 185°-187° C. Analysis: Calculated for C12H10ClN3O: % C, 58.2; % H, 4.1; N, 17.0; Found: % C, 58.0; % H, 4.0; % N, 17.3.

Workup

filtrationwas then filtered
customfinally evaporated to low volume
additionThe slurry was mixed with diethyl ether
customthe solid was separated by filtration
washwashed with ether
customrecrystallized from methanol

Sources & evidence

ORD record: ord-09412f2ea4984b9680a422f7d8c6366d
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04689338

Reaction notes

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