Ethyl acetate hexane → HCID 178467004, compound
Reaction equation
C(O[C:4](=[O:20])[CH2:5][C:6]([O:17][CH2:18][CH3:19])=[N:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=1[CH3:16])C.CCOC(C)=O.CCCCCC>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:18]([O:17][C:6]1[CH:5]=[C:4]([OH:20])[C:13]2[C:8](=[C:9]([CH3:16])[C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[N:7]=1)[CH3:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Ethoxy-3-(3-methoxy-2-methyl-phenylimino)-propionic acid ethyl ester (1.56 g, 5.57 mmol) was dissolved in diphenyl ether then placed in a 300° C. sand bath. The internal temperature was kept between 240-250° C. for 15 minutes then the reaction was cooled to room temperature. The crude material was directly loaded onto a silica gel column (0→60% EtOAc/hexane) to afford 2-ethoxy-7-methoxy-8-methyl-quinolin-4-ol (882 mg, 68%). LCMS found 234.1 [M+H]+.