C(O)(=O)C.[N:5]1[C:14]2[CH:13]=[CH:12][CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-].[Na+].[OH-].[Na+]>CO.O>[C:16]1([NH:15][CH:12]2[CH2:13][C:14]3[N:5]=[CH:6][CH:7]=[CH:8][C:9]=3[CH2:10][CH2:11]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
Glacial acetic acid (1.2 ml, 20 mmol) was added dropwise to a stirred solution of 5,6-dihydroquinoline (1.31 g, 10 mmol) and aniline (1.86 g, 20 mmol) in methanol (4 ml). The solution was heated under reflux for 21h, cooled to room temperature, poured onto a mixture of saturated aqueous sodium chloride (25 ml) and water (25 ml), and the mixture was basified with 10N-NaOH and extracted with ether (3×25 ml). The extracts were concentrated in vacuo to give a dark orange oil which was chromatographed [alumina; ethyl acetate-toluene (1:24 to 1:4)] to give a solid. Recrystallisation from di-isopropyl ether gave the product (1.50 g), mp 102°-103°. (Found: C, 80.4; H, 76.2; N, 12.5. C15H16N2 requires C, 80.3; H, 7.2; N, 12.5%)
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