Piperidine → HCID 9863633, compound

HRID 1647712Notes

Reaction equation

HRID 1647712 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[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:3]3[C:8](=[CH:9][CH:10]=[C:11]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])[CH:7]=[N:6][CH:5]=[CH:4]3

Participants

5

Reactant 3

HCID 8082PiperidineHCID 30386Isoquinolin-5-olHCID 219691[(3,4-Dimethoxyphenyl)methylidene]propanedinitrile

Product 1

HCID 9863633HCID 9863633, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of 5-hydroxyisoquinoline (2.90 g) and 3,4-dimethoxy benzylidenemalononitrile (4.28 g) in ethanol (11 ml) was added dropwise piperidine (1.70 g). The suspension was then heated at reflux temperature for one hour forming a red solution. This was then allowed to cool to room temperature, depositing a brown solid. This 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[2,3-f] isoquinoline-3-carbonitrile as a yellow-brown solid, m.p. 225°-228° C.

Workup

  1. temperatureThe suspension was then heated
  2. temperatureat reflux temperature for one hour
  3. customforming a red solution
  4. filtrationThis was filtered off
  5. washwashed with ethanol and ether
  6. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-049a88eba40a43aca12f9e9b6421a261
Source dataset
uspto-grants-1995_07
Patent number
US05434160

Reaction notes

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