Potassium Carbonate → 3-(N-methyl-2-pyrroyl)-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylic acid

HRID 648015Notes

Reaction equation

HRID 648015 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([C:9]1[N:13]2[CH2:14][CH2:15][CH2:16][CH:17]([C:18]([O:20]C(C)C)=[O:19])[C:12]2=[CH:11][CH:10]=1)=[O:8].C(=O)([O-])[O-].[K+].[K+]>CO.O>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([C:9]1[N:13]2[CH2:14][CH2:15][CH2:16][CH:17]([C:18]([OH:20])=[O:19])[C:12]2=[CH:11][CH:10]=1)=[O:8]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 70534455isopropyl 3-(N-methyl-2-pyrroyl)-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate

Product 1

HCID 705349973-(N-methyl-2-pyrroyl)-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of 0.314 g. of isopropyl 3-(N-methyl-2-pyrroyl)-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate, 0.28 g. of potassium carbonate and 10 ml. of a (1:1) methanol-water mixture is refluxed under nitrogen atmosphere for 3 hours, cooled, and evaporated to dryness. The residue is taken up in 50 ml. of water and extracted with ethyl acetate (3×10 ml.). The aqueous solution is acidified with 10% hydrochloric acid and extracted with ethyl acetate (10×15 ml.). The combined extracts are washed with saturated sodium chloride solution dried with anhydrous sodium sulfate and evaporated to dryness under reduced pressure, to afford 3-(N-methyl-2-pyrroyl)-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylic acid, (XIVa, R=H, Q=CH3, n=2).

Workup

  1. additionA mixture of 0.314 g
  2. temperaturecooled
  3. customevaporated to dryness
  4. extractionof water and extracted with ethyl acetate (3×10 ml.)
  5. extractionextracted with ethyl acetate (10×15 ml.)
  6. washThe combined extracts are washed with saturated sodium chloride solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4580b549d5d34e7b8244d4b332589f46
Source dataset
uspto-grants-1983_10
Patent number
US04410534

Reaction notes

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