8-Hydroxyquinoline → HCID 3165203, compound

HRID 1647713Notes

Reaction equation

HRID 1647713 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

5

Reactant 3

HCID 19238-HydroxyquinolineHCID 8082PiperidineHCID 219691[(3,4-Dimethoxyphenyl)methylidene]propanedinitrile

Product 1

HCID 3165203HCID 3165203, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. temperatureThis mixture was then heated
  2. temperatureat reflux for 90 minutes
  3. temperatureto cool to room temperature overnight
  4. filtrationThe precipitated orange solid was filtered off
  5. washwashed with ethanol and ether
  6. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-1d5038a04a364041bf9df6d16787d54a
Source dataset
uspto-grants-1995_07
Patent number
US05434160

Reaction notes

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