Water → HCID 15581187, compound

HRID 1283125Notes

Reaction equation

HRID 1283125 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][C:8]3[CH:14]=[C:13]([CH:15](C#N)[C:16](=[O:24])[CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])[CH:12]=[CH:11][C:9]=3[O:10][C:2]=12.O.[OH-].[Na+]>Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][C:8]3[CH:14]=[C:13]([CH2:15][C:16](=[O:24])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:12]=[CH:11][C:9]=3[O:10][C:2]=12

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21519379HCID 21519379, compound

Product 1

HCID 15581187HCID 15581187, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4.8 g of ethyl 5(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)-5-cyano-4-oxovalerate is dissolved in 10 ml of concentrated hydrochloric acid. 30 ml of water is added at a stretch to the solution with stirring under ice-cooling, and the mixture is stirred under reflux for 5 hours. The reaction mixture is ice-cooled and adjusted to approximately pH 3 by addition of 30% sodium hydroxide. The resulting oil layer is extracted with chloroform, and the extract is dried over anhydrous sodium sulfate and concentrated. The oily residue, on standing, becomes solid. The solid is recrystallized from a mixture of dioxane and water (1:1) to give 3.4 g of 5-(5H-[1]benzopyrano[2,3-b]pyridin-7-yl)-4-oxovaleric acid as white needles melting at 146°-147°C.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred
  3. temperatureunder reflux for 5 hours
  4. temperaturecooled
  5. extractionThe resulting oil layer is extracted with chloroform
  6. dry with materialthe extract is dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe solid is recrystallized from a mixture of dioxane and water (1:1)

Sources & evidence

ORD record
ord-ae63add7533d4427a35d4894ebf683f8
Source dataset
uspto-grants-1976_08
Patent number
US03974168

Reaction notes

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