Thionyl Chloride → 2-Chloromethyl-1-phenylmethyl-1H-imidazo[4,5-c]quinolin-4-amine Hydrochloride
Reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:22]O)[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.S(Cl)([Cl:26])=O>>[ClH:26].[Cl:26][CH2:22][C:13]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=1Participants
3
Procedure
4-Amino-1-phenylmethyl-1H-imidazo[4,5-c]quinoline-2-methanol (2.0 g; 0.0066 mol, Example 27) was added in small portions to thionyl chloride (10 mL). After stirring at room temperature for 30 min the product had crystallized from solution. The mixture was diluted with dry ether (75 mL). The solid was filtered from the mixture, washed with ether, and thoroughly dried. The product was used as such without further characterization or purification.
Workup
- customhad crystallized from solution
- additionThe mixture was diluted with dry ether (75 mL)
- filtrationThe solid was filtered from the mixture