Methanol → 3-(2-Thenoyl)-2-methyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylic acid

HRID 648013Notes

Reaction equation

HRID 648013 reaction equation
[C:1]1([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][C:9]=2[CH3:23])=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.CO.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]1([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][C:9]=2[CH3:23])=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 20483691Isopropyl 3-(2-thenoyl)-2-methyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate

Product 1

HCID 204837813-(2-Thenoyl)-2-methyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 900 mg. of isopropyl 3-(2-thenoyl)-2-methyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate in 15 ml. of methanol is treated with a solution of 125 g. of potassium carbonate in 10 ml. of water. The reaction mixture is refluxed under nitrogen atmosphere for 3 hours, cooled, and evaporated to dryness. The residue is taken up in 50 ml. of water, cooled to 0° and made acidic with 10% aqueous hydrochloric acid. The resultant mixture is extracted with ethyl acetate (3×50 ml.). The extracts are dried over magnesium sulfate and evaporated to dryness under reduced pressure, to give 3-(2-thenoyl)-2-methyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylic acid (XIIa, R=CH3, M=H, X=S, n=1).

Workup

  1. temperatureThe reaction mixture is refluxed under nitrogen atmosphere for 3 hours
  2. temperaturecooled
  3. customevaporated to dryness
  4. temperatureof water, cooled to 0°
  5. extractionThe resultant mixture is extracted with ethyl acetate (3×50 ml.)
  6. dry with materialThe extracts are dried over magnesium sulfate
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1b5f1422bc18426d9b6598d521a48b7b
Source dataset
uspto-grants-1983_10
Patent number
US04410534

Reaction notes

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