Ethyl cyanoacetate → HCID 178509384, compound

HRID 47060

Reaction equation

HRID 47060 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:10]([CH2:12][C:13](OCC)=[O:14])#[N:11].N1CCCCC1>C(O)C>[OH:14][C:13]1[C:12]([C:10]#[N:11])=[CH:4][C:3]2[C:2](=[N:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 178509384HCID 178509384, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-aminonicotinaldehyde (2.44 g., 0.02 m), ethyl α-cyanoacetate (4.52 g., 0.04 m.), absolute ethanol (50 ml.) and piperidine (0.5 ml) is stirred under reflux. After 1 hour, the solution is cooled to 0°-4° C. The yellow solid is filtered and dried to yield 2.5 g. (73%) of 2-hydroxy-3-cyano-1,8-naphthyridines, m.p. 300° C.

Workup

  1. temperatureunder reflux
  2. temperaturethe solution is cooled to 0°-4° C
  3. filtrationThe yellow solid is filtered
  4. customdried
  5. customto yield 2.5 g

Sources & evidence

ORD record
ord-2e9252f1b37d4a8f95e6b4a6feb9158b
Source dataset
uspto-grants-1979_11
Patent number
US04176183

Linked notes

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