Acetic Acid → MLS003115531

HRID 1579438Notes

Reaction equation

HRID 1579438 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[CH2:9][C:8]=2[CH:17]=1)#N.[C:18]([OH:21])(=[O:20])[CH3:19]>Cl>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]2[CH2:9][C:8]3[CH:17]=[C:4]([CH2:19][C:18]([OH:21])=[O:20])[CH:5]=[CH:6][C:7]=3[O:16][C:11]=12

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 12274195HCID 12274195, compound

Product 1

HCID 323005MLS003115531

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 11.5 g of 7-cyanomethyl-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 for 24 hours. After concentration, water is added to the residue, and further 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. The crystals are recrystallized from dioxane to give 8.5 g of 5H-[1]benzopyrano[2,3-b]-pyridin-7-yl-acetic acid as white needles melting at 218°C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 24 hours
  3. concentrationAfter concentration, water
  4. additionis added to the residue, and further 10% sodium hydroxide solution
  5. additionis 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. customThe crystals are recrystallized from dioxane

Sources & evidence

ORD record
ord-182892d7f348424fa54a2ff801de0448
Source dataset
uspto-grants-1976_01
Patent number
US03931205

Reaction notes

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