Ethyl cyanoacetate → HCID 15598959, compound

HRID 986755Notes

Reaction equation

HRID 986755 reaction equation
[OH:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH:12]=[C:11]([C:14]#N)[C:10](=[O:16])[C:9]=2[CH:17]=1)([CH3:4])[CH3:3].[C:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])#[N:19].[NH:26]1CCCCC1>C(O)C>[NH2:19][C:18]1[N:26]=[C:12]2[O:13][C:8]3[CH:7]=[CH:6][C:5]([C:2]([OH:1])([CH3:4])[CH3:3])=[CH:17][C:9]=3[C:10](=[O:16])[C:11]2=[CH:14][C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 13728614HCID 13728614, compound

Product 1

HCID 15598959HCID 15598959, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 6-(1-hydroxy-1-methylethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile (4.7 g), ethyl cyanoacetate (2.5 g) and ethanol (100 ml) was added piperidine (1.9 g), which was refluxed for 3 hours, then cooled. The precipitating crystals were collected by filtration. The crystals were dissolved in chloroform, which was subjected to a silica-gel (120 g) column chromatography using chloroform-acetone-formic acid (90:10:1) as the eluent. The solvent was evaporated off. To the residue was added ethanol, and sparingly soluble matter was collected by filtration, which was recrystallized from chloroform to give colorless needles (4.86 g) of ethyl 2-amino-7-(1-hydroxy-1-methylethyl)-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylate, m.p. 263°-264° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperaturecooled
  3. filtrationThe precipitating crystals were collected by filtration
  4. dissolutionThe crystals were dissolved in chloroform
  5. customThe solvent was evaporated off
  6. additionTo the residue was added ethanol, and sparingly soluble matter
  7. filtrationwas collected by filtration, which
  8. customwas recrystallized from chloroform

Sources & evidence

ORD record
ord-18fa059d54ba47afa1cd46e15b353f2f
Source dataset
uspto-grants-1987_12
Patent number
US04716167

Reaction notes

Loading…