Methanol → HCID 70534795, compound

HRID 648016Notes

Reaction equation

HRID 648016 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([CH:9]1[N:14]2[CH:15]=[C:16]([CH3:18])[CH:17]=[C:13]2[CH:12]([C:19]([O:21]C(C)C)=[O:20])[CH2:11][CH2:10]1)=[O:8].CO.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([CH:9]1[N:14]2[CH:15]=[C:16]([CH3:18])[CH:17]=[C:13]2[CH:12]([C:19]([OH:21])=[O:20])[CH2:11][CH2:10]1)=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 70534754HCID 70534754, compound

Product 1

HCID 70534795HCID 70534795, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 328 mg. of isopropyl 5-(N-methyl-2-pyrroyl)-2-methyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate in 5 ml. of methanol is treated with a solution of 0.28 g. of potassium carbonate in 5 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°, made acidic with 10% hydrochloric acid and the resultant mixture extracted with ethyl acetate (3×50 ml.). The combined extracts are dried over magnesium sulfate and evaporated to dryness under reduced pressure, to give 5-(N-methyl-2-pyrroyl)-2-methyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylic acid (XIVa, R and Q=CH3, 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 extracted with ethyl acetate (3×50 ml.)
  6. dry with materialThe combined extracts are dried over magnesium sulfate
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9f74e3502909454ea62c43944e3e17ba
Source dataset
uspto-grants-1983_10
Patent number
US04410534

Reaction notes

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