Ethyl cyanoacetate → HCID 13728611, compound

HRID 986756Notes

Reaction equation

HRID 986756 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH:11]=[C:10]([C:13]#N)[C:9](=[O:15])[C:8]=2[CH:16]=1)(=[O:3])[CH3:2].[C:17]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])#[N:18].[NH:25]1CCCCC1>C(O)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]3=[N:18][C:17]([NH2:25])=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:13]=[C:10]3[C:9](=[O:15])[C:8]=2[CH:16]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 137286106-Acetyl-4-oxo-4H-1-benzopyran-3-carbonitrile

Product 1

HCID 13728611HCID 13728611, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (800 ml) was suspended 6-acetyl-4-oxo-4H-1-benzopyran-3-carbonitrile (32 g). To the suspension were added ethyl cyanoacetate (23.9 ml) and piperidine (23.7 ml). The mixture was refluxed for one hour, then cooled to room temperature. The resulting crystals were collected by filtration, washed with ethanol, then with acetone, followed by drying to give ethyl 7-acetyl-2-amino-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylate as yellow crystals (46.3 g). Melting point: >300° C.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. filtrationThe resulting crystals were collected by filtration
  3. washwashed with ethanol
  4. customby drying

Sources & evidence

ORD record
ord-8e835ff05a3c47818bffba484b806547
Source dataset
uspto-grants-1987_12
Patent number
US04716167

Reaction notes

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