Hydrochloric Acid → 2-(5-oxo-5H-chromeno[2,3-b]pyridin-7-yl)propanoic acid

HRID 1579447Notes

Reaction equation

HRID 1579447 reaction equation
[C:1]([C:3]([C:10]1[CH:11]=[CH:12][C:13]2[O:22][C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[C:15](=[O:23])[C:14]=2[CH:24]=1)(C)[C:4]([O:6]CC)=[O:5])#N.Cl>C(O)(=O)C>[O:23]=[C:15]1[C:16]2[C:17](=[N:18][CH:19]=[CH:20][CH:21]=2)[O:22][C:13]2[CH:12]=[CH:11][C:10]([CH:3]([CH3:1])[C:4]([OH:6])=[O:5])=[CH:24][C:14]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21568519Ethyl 2-cyano-2-(5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-7-yl)propanoate

Product 1

HCID 122741862-(5-oxo-5H-chromeno[2,3-b]pyridin-7-yl)propanoic acidYield 79.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 16.5 g of ethyl 2-cyano-2-(5-oxo-5H-[1]benzopyrano-[2,3-b]pyridin-7-yl)propionate, 80 ml of acetic acid and 35 ml of concentrated hydrochloric acid is heated under reflux for 24 hours. After concentration, water is added to the residue, and further a 10% sodium hydroxide solution is added to dissolve the residue. An insoluble material is removed by extraction with chloroform. The aqueous layer is made acid with acetic acid, and the crystalline precipitate is collected and recrystallized from aqueous dioxane to give 11 g of 2-(5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-7-yl)propionic acid as white needles melting at 194°-195°C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 24 hours
  3. concentrationAfter concentration, water
  4. additionis added to the residue
  5. additionfurther a 10% sodium hydroxide solution is added
  6. dissolutionto dissolve the residue
  7. customAn insoluble material is removed by extraction with chloroform
  8. customthe crystalline precipitate is collected
  9. customrecrystallized from aqueous dioxane

Sources & evidence

ORD record
ord-af16e595e58d40709ffa73c54e7cb429
Source dataset
uspto-grants-1976_01
Patent number
US03931205

Reaction notes

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