Ethyl Acetate → HCID 58149933, compound

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH:19]=[CH:20][N+:21]([O-])=[CH:22]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].Cl[C:29]1C=CC2C(=CC=CC=2)N=1.[C:39]([O:42][CH2:43][CH3:44])(=[O:41])[CH3:40]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH:19]=[CH:20][N:21]=[C:22]4[CH2:29][CH2:40][C:39]([O:42][CH2:43][CH3:44])=[O:41])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

Procedure

The contents of the three vials were pooled with the reaction mixture from a previous preparation of D6 (using the same method and 100 mg of chloroquinoline starting material), and the mixture diluted with ethyl acetate and washed sequentially with brine (×2) and water (×2). The organic layers were concentrated in vacuo to give a red oil that was dissolved in dichloromethane, and purified by flash chromatography on silica gel, eluting with a dichloromethane/ethyl acetate (2% to 20% EtOAc) gradient. The relevant fractions were pooled and concentrated in vacuo to give a red solid that was triturated with diethyl ether. The resulting brick coloured solid was collected by filtration and dried in vacuo to give the title compound (80 mg, 8%).