Acetic Acid → HCID 12274185, compound

HRID 1579442Notes

Reaction equation

HRID 1579442 reaction equation
C(C[C:4]1[CH:5]=[CH:6][C:7]2[O:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[C:9](=[O:17])[C:8]=2[CH:18]=1)#N.[C:19]([OH:22])(=[O:21])[CH3:20]>Cl>[O:17]=[C:9]1[C:10]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[O:16][C:7]2[CH:6]=[CH:5][C:4]([CH2:20][C:19]([OH:22])=[O:21])=[CH:18][C:8]1=2

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 12274184HCID 12274184, compound

Product 1

HCID 12274185HCID 12274185, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 12 g of 7-cyanomethyl-5-oxo-5H-[1]benzopyrano[2,3-b]-pyridine in a mixture of 60 ml of acetic acid and 25 ml of concentrated hydrochloric acid is heated under reflux on an oil bath 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 resulting crystalline precipitate is filtered off and recrystallized from aqueous dimethylformamide to give 8.6 g of 5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-7-yl-acetic acid as white needles melting at 244°- 245°C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux on an oil bath 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. filtrationthe resulting crystalline precipitate is filtered off
  9. customrecrystallized from aqueous dimethylformamide

Sources & evidence

ORD record
ord-de5b21b15196437f859268de3411c8de
Source dataset
uspto-grants-1976_01
Patent number
US03931205

Reaction notes

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