Phosphorus oxychloride → 1-(2-benzoyloxyethyl)-4-chloro-1H-imidazo[4,5-c]quinoline
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]([O-])=[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.P(Cl)(Cl)([Cl:28])=O>>[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]=[C:16]([Cl:28])[C:15]=2[N:14]=[CH:13]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
A mixture of 50g (0.15 mole) of 1-(2-benzoyloxyethyl)-1H-imidazo[4,5-c]quinolin-5-oxide (from Example 116) and 200 ml of phosphorus oxychloride was heated for two hours on a steam bath. The mixture was then partially evaporated in vacuo. The mixture was poured over ice, and the solution was neutralized with sodium hydroxide. The product was separated by filtration and dissolved in dichloromethane, and the solution was washed with aqueous sodium bicarbonate solution and dried. Evaporation provided a solid which was recrystallized from a 50:50 methanol:dichloromethane solution to provide white 1-(2-benzoyloxyethyl)-4-chloro-1H-imidazo[4,5-c]quinoline, m.p. 186°-190,C. Analysis: Calculated for C19H14ClN3O2 ; % C, 64.9; % H, 4.0; % N, 12.0; Found: % C, 64.8; % H, 3.8; % N, 12.1.
Workup
- temperaturewas heated for two hours on a steam bath
- customThe mixture was then partially evaporated in vacuo
- additionThe mixture was poured over ice
- customThe product was separated by filtration
- dissolutiondissolved in dichloromethane
- washthe solution was washed with aqueous sodium bicarbonate solution
- customdried
- customEvaporation
- customprovided a solid which
- customwas recrystallized from a 50:50 methanol
Sources & evidence
- ORD record
- ord-fd07e5c4703549e79fcc07e18a5b58b2
- Source dataset
- uspto-grants-1987_08
- Patent number
- US04689338
Reaction notes
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