[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].Cl.[CH:10](=O)/[CH:11]=[CH:12]/[CH3:13].[OH-].[Na+]>O>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:3]=1[N:4]=[C:12]([CH3:13])[CH:11]=[CH:10]2A mixture consisting of 128 g (1.0 mole) of o-chloroaniline, 304 g of conc. hydrochloric acid and 61 g of water was maintained at 90°-95° C., and with sufficient stirring, 70 g (1.0 mole) of crotonaldehyde was added dropwise over the course of 2 hours. After the addition, the mixture was reacted further at 90°-95° C. for 1 hour. The reaction mixture was cooled, and then rendered alkaline by adding a conc. aqueous solution containing 132 g of sodium hydroxide with ice cooling. The alkaline mixture was separated into layers, and the oily layer was distilled at 2-3 mmHg to afford 72 g (0.4 mole) of 8-chloroquinaldine.
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