OC1CCN([C:8]2[C:9]([N+:16]([O-:18])=[O:17])=[C:10]([CH:13]=[CH:14][CH:15]=2)C=O)CC1.[Na+].[C:20]([O:26][CH2:27][CH3:28])(=[O:25])[CH2:21][C:22]([O-])=O.S(=O)(=O)(O)[OH:30].[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>N1C=CC=CC=1>[OH:30][CH:37]1[CH2:38][CH2:39][N:34]([C:14]2[CH:15]=[CH:8][C:9]([N+:16]([O-:18])=[O:17])=[C:10]([CH:13]=2)[CH:22]=[CH:21][C:20]([O:26][CH2:27][CH3:28])=[O:25])[CH2:35][CH2:36]1To a solution of 10.1 g of 5 (4-hydroxypiperidino)-2-nitrobenzaldehyde and 34.4 g of ethyl malonate sodium salt in 120 ml of pyridine were added 9.9 g of concentrated sulfuric acid and 850 mg of piperidine. After refluxing for 1 hr, the reaction mixture was concentrated under a reduced pressure. Dilute hydrochloric acid was added to the residue and it was extracted with chloroform. The extract was washed with water, dried, and evaporated under a reduced pressure. The residue was purified by a silica gel column chromatography to give 10.6 g of ethyl 5-(4-hydroxypiperidino)-2-nitrocinnamate.
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