Ammonium Hydroxide → 4-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline hydrate

HRID 255552Notes

Reaction equation

P(Cl)(Cl)([Cl:3])=[O:2].[CH2:6]([N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N+:15]([O-])=[CH:14][C:13]=2[N:12]=[CH:11]1)[CH:7]([CH3:9])[CH3:8].[OH-].[NH4+]>CN(C)C=O>[OH2:2].[Cl:3][C:14]1[C:13]2[N:12]=[CH:11][N:10]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:22]=2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 4.8 g (0.0311 mole) of phosphorus oxychloride in 20 ml of N,N-dimethylformamide was added, in small portions, 5.0 g (0.207 mole) of 1-isobutyl-1H-imidazo[4,5-c]quinoline-5-oxide. The solution was stirred for 15 minutes at 20° C., then heated on a steam bath for 15 minutes. The solution was cooled to 20° C., then poured into stirred ice. The solution was basified to pH 8 with concentrated ammonium hydroxide. The yellow solid precipitate was separated by filtration, washed sequentially with water and diethyl ether, and dried to provide 4-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline hydrate, m.p. 103°-107° C. Recrystallization twice from ethyl acetate with drying provided 4-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline, m.p. 135°-137° C. Analysis: Calculated for C14H14ClN3 : %C, 64.7; %H, 5.4; %N, 16.2; Found: %C, 64.6; %H, 5.5; %N, 16.1.

Workup

temperatureheated on a steam bath for 15 minutes
temperatureThe solution was cooled to 20° C.
additionpoured
stirringinto stirred ice
customThe yellow solid precipitate was separated by filtration
washwashed sequentially with water and diethyl ether
customdried

Sources & evidence

ORD record: ord-43bfc5f4ff3b4830b29bb8b70858a7f2
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04698348

Reaction notes

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