4-Amino-m-cresol → Ethyl 3-methoxy-7-(4-hydroxy-2-methylphenylamino)thieno-[3,2-b]pyridine-6-carboxylate hydrochloride
Reaction equation
[CH3:1][O:2][C:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11]([Cl:12])=[C:6]2[S:5][CH:4]=1.[OH:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[C:21]([CH3:26])[CH:20]=1>C1(OC)C=CC=CC=1>[ClH:12].[CH3:1][O:2][C:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11]([NH:23][C:22]3[CH:24]=[CH:25][C:19]([OH:18])=[CH:20][C:21]=3[CH3:26])=[C:6]2[S:5][CH:4]=1Participants
4
Procedure
Ethyl 3-methoxy-7-chlorothieno[3,2-b]pyridine-6-carboxylate (1.5 g, 0.0055 mol) and 4-hydroxy-2-methylaniline (1.36 g, 0.011 mol) in anisole (30 ml) were heated under reflux in an inert atmosphere for thirty hours. The solid obtained on cooling was collected by filtration and recrystallised from ethanol to give a brown crystalline solid, 1.09 g. Recrystallisation from ethanol after filtration through charcoal gave the title compound, 0.63 g, m.p. 286°-288°.