Ethanol → HCID 13192925, compound

HRID 1579399Notes

Reaction equation

HRID 1579399 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4]2[CH:12]=[CH:13][C:14]([C:16]([OH:18])=[O:17])=[CH:15][C:3]1=2.[CH2:19](O)[CH3:20]>>[O:1]=[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4]2[CH:12]=[CH:13][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:15][C:3]1=2

Participants

3

Reactant 2

HCID 702EthanolHCID 12202680HCID 12202680, compound

Product 1

HCID 13192925HCID 13192925, compound

Procedure

A mixture of 10.5 g of 5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-7-carboxylic acid and 150 ml of ethanol is allowed to absorb 10 g of hydrogen chloride gas, and then refluxed for 16 hours. The ethanol is distilled off, and water is added to the crystalline residue. The mixture is extracted with chloroform, and the chloroform layer is washed with aqueous potassium carbonate solution and dried. The chloroform is distilled off, and the residue is recrystallized from ethanol to give ethyl 5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-7-carboxylate melting at 131°-132°C.

Workup

  1. customto absorb 10 g of hydrogen chloride gas
  2. temperaturerefluxed for 16 hours
  3. distillationThe ethanol is distilled off
  4. additionwater is added to the crystalline residue
  5. extractionThe mixture is extracted with chloroform
  6. washthe chloroform layer is washed with aqueous potassium carbonate solution
  7. customdried
  8. distillationThe chloroform is distilled off
  9. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-047666cf9ce14b1cb66088f405756036
Source dataset
uspto-grants-1976_01
Patent number
US03931199

Reaction notes

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