Methanol → HCID 12795087, compound

HRID 647995Notes

Reaction equation

HRID 647995 reaction equation
[C:1]1([C:14]([O:16]C)=[O:15])[CH:2]=[CH:3][N:4]2[CH2:9][CH2:8][CH2:7][CH:6]([C:10]([O:12]C)=[O:11])[C:5]=12.CO.[OH-].[K+]>O>[C:1]1([C:14]([OH:16])=[O:15])[CH:2]=[CH:3][N:4]2[CH2:9][CH2:8][CH2:7][CH:6]([C:10]([OH:12])=[O:11])[C:5]=12

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 12795068HCID 12795068, compound

Product 1

HCID 12795087HCID 12795087, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8.6 g. of dimethyl 5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-1,8-dicarboxylate in 100 ml. of methanol is treated with a solution of 9.0 g. of potassium hydroxide in 100 ml. of water, and the reaction mixture is refluxed for 24 hours. The cooled solution is evaporated to dryness at a temperature of 30° C. and the residue is dissolved in the minimum amount of saturated sodium chloride solution. The resultant solution is acidified with concentrated hydrochloric acid and the precipitated solid is collected by filtration, washed with water and dried in vacuo. The mother liquor is extracted with ethyl acetate 3 times and the combined extracts are dried over magnesium sulfate and evaporated to dryness under reduced pressure and recrystallization of the combined residues from methanol yields 5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-1,8-dicarboxylic acid (VIII, R=H, n=1), m.p. 236°-237° C.

Workup

  1. customThe cooled solution is evaporated to dryness at a temperature of 30° C.
  2. dissolutionthe residue is dissolved in the minimum amount of saturated sodium chloride solution
  3. filtrationthe precipitated solid is collected by filtration
  4. washwashed with water
  5. customdried in vacuo
  6. extractionThe mother liquor is extracted with ethyl acetate 3 times
  7. dry with materialthe combined extracts are dried over magnesium sulfate
  8. customevaporated to dryness under reduced pressure and recrystallization of the combined residues from methanol

Sources & evidence

ORD record
ord-84c9b9d34c45491fb2ae7a12ac8e164e
Source dataset
uspto-grants-1983_10
Patent number
US04410534

Reaction notes

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