Dichloromethane → HCID 19026199, compound

Reaction equation

[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]1([CH2:14][O:15][NH:16][CH:17]2[CH2:26][CH2:25][CH2:24][C:23]3[N:22]=[C:21]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:20]=[CH:19][C:18]2=3)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:35]CCl>>[ClH:35].[C:8]1([CH2:14][O:15][N:16]([CH:17]2[CH2:26][CH2:25][CH2:24][C:23]3[N:22]=[C:21]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:20]=[CH:19][C:18]2=3)[C:1](=[O:3])[CH3:2])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Reactant 3

HCID 6344Dichloromethane2×

HCID 7918Acetic Anhydride

HCID 19026180HCID 19026180, compound

Product 1

HCID 19026199HCID 19026199, compoundYield 52%

Procedure

Acetic anhydride (3.77 g) was added to a solution of N,N-dimethylaminopyridine (0.2 g), N,2-bis(phenylmethoxy)-5,6,7,8-tetrahydro-5-quinolinamine (12.1 g) and dichloromethane (170 ml) at room temperature. The mixture was stirred at room temperature for 48 hrs, diluted with dichloromethane, and extracted with saturated sodium bicarbonate solution. The combined extracts were washed with water, brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was dissolved in methanol and acidified with 2-propanol/hydrochloric acid solution. The mixture was evaporated and the residue was recrystallized from ethanol/ethyl acetate to give 7.64 g (52%) of product, mp 125°-126° C.