[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH3:5].[NH:7]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][N:10]=1)[NH2:8].Cl>CCOCC>[CH:1](=[N:8][NH:7][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][N:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5]Valeraldehyde (5.14 g.) was added to a refluxing solution of 1-hydrazino-3,4-dihydroisoquinoline (8 g.) in ether (300 ml.). The mixture was allowed to stand (for 45 min.) at room temperature. Ethereal hydrochloric acid was added. Recrystallization of the resulting solid from ethanol-ether gave 1-(2-pentylidenehydrazino)-3,4-dihydroisoquinoline (I: X=CH3 (CH2)3, X'=Y=Y'=Z=Z'=H) hydrochloride in two crops (11.6 g. and 0.2 g., m.p. 147°-148° C.).
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