8-Hydroxyquinoline → HCID 3165203, compound

Reaction equation

[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[CH:17]=[C:18]([C:21]#[N:22])[C:19]#[N:20].N1CCCCC1>C(O)C>[NH2:22][C:21]1[O:1][C:2]2[C:11]3[N:10]=[CH:9][CH:8]=[CH:7][C:6]=3[CH:5]=[CH:4][C:3]=2[CH:17]([C:16]2[CH:23]=[CH:24][C:25]([O:26][CH3:27])=[C:14]([O:13][CH3:12])[CH:15]=2)[C:18]=1[C:19]#[N:20]

Participants

Procedure

A stirred suspension of 8-hydroxyquinoline (2.90 g) and 3,4-dimethoxy benzylidenemalononitrile(4.28 g) in ethanol (15 ml) was treated with piperidine (1.70 g) and the suspension stirred at room temperature for one hour. This mixture was then heated at reflux for 90 minutes. The red solution was then allowed to cool to room temperature overnight. The precipitated orange solid was filtered off and washed with ethanol and ether and dried in vacuo at 60° C., yielding 2-amino-4-(3,4-dimethoxyphenyl)-4H-pyrano[3,2-h]quinoline-3-carbonitrile as a tan solid, m.p. 118°-120° C.