Sodium Hydroxide → 3-p-Fluorobenzoyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylic acid

HRID 647998Notes

Reaction equation

HRID 647998 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[N:12]3[CH2:13][CH2:14][CH2:15][CH:16]([C:17]([O:19]C(C)C)=[O:18])[C:11]3=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[N:12]3[CH2:13][CH2:14][CH2:15][CH:16]([C:17]([OH:19])=[O:18])[C:11]3=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20484013Isopropyl 3-p-fluorobenzoyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate

Product 1

HCID 134870783-p-Fluorobenzoyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of isopropyl 3-p-fluorobenzoyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate in methanol is treated under an atmosphere of nitrogen with a solution of sodium hydroxide in water, maintaining the reaction mixture at room temperature for 1.5 hours. The methanol is then removed under reduced pressure and the basic solution which remains is diluted with water and extracted with ether to remove any unsaponifiable product. The aqueous solution is acidified with 10% hydrochloric acid and extracted three times with ethyl acetate. The combined extracts are dried and evaporated to dryness under reduced pressure, and the residue crystallized from ethyl acetate-hexane, to give 3-p-fluorobenzoyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylic acid, identical to the product obtained in Example 8.

Workup

  1. customThe methanol is then removed under reduced pressure
  2. additionthe basic solution which remains is diluted with water
  3. extractionextracted with ether
  4. customto remove any unsaponifiable product
  5. extractionextracted three times with ethyl acetate
  6. customThe combined extracts are dried
  7. customevaporated to dryness under reduced pressure
  8. customthe residue crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-499745b9ed0e44d98cd9aa4e6e73ca44
Source dataset
uspto-grants-1983_10
Patent number
US04410534

Reaction notes

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