Hydrochloric Acid → 5-(Benzyloxy)-1,4-dihydro-4-oxo-2-pyridinecarboxylic acid, ethyl ester

HRID 1249599Notes

Reaction equation

HRID 1249599 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:18])[CH:11]=[C:12]([C:15]([OH:17])=[O:16])[NH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:20](O)[CH3:21]>>[CH2:1]([O:8][C:9]1[C:10](=[O:18])[CH:11]=[C:12]([C:15]([O:17][CH2:20][CH3:21])=[O:16])[NH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 110539185-(Benzyloxy)-4-oxo-1,4-dihydropyridine-2-carboxylic acid

Product 1

HCID 867411755-(Benzyloxy)-1,4-dihydro-4-oxo-2-pyridinecarboxylic acid, ethyl ester

Conditions

Temperature
0 °C

Procedure

A suspension of 5-(benzyloxy)-1,4-dihydro-4-oxo-2-pyridinecarboxylic acid (8.24 g, 33.6 mmole) in 120 ml of ethanol was cooled to 0° C. and treated with a stream of dry HCl for 15 minutes. The resulting mixture was heated at 50° C. for 5.5 hours. The volatiles were removed in vacuo and the residue was treated with water. While cooling, the pH was raised to 7 with saturated potassium bicarbonate and the resulting mixture was extracted with dichloromethane. The extracts were washed with brine and dried over sodium sulfate. Filtration and concentration in vacuo produced 7.32 g of the title compound.

Workup

  1. temperatureThe resulting mixture was heated at 50° C. for 5.5 hours
  2. customThe volatiles were removed in vacuo
  3. additionthe residue was treated with water
  4. temperatureWhile cooling
  5. temperaturethe pH was raised to 7 with saturated potassium bicarbonate
  6. extractionthe resulting mixture was extracted with dichloromethane
  7. washThe extracts were washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-e203bfe1caa14ae380bfdf1818689db8
Source dataset
uspto-grants-1986_12
Patent number
US04632985

Reaction notes

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