Methanol → HCID 13649429, compound

HRID 280206Notes

Reaction equation

HRID 280206 reaction equation
[C:1]([C:5](=[CH2:22])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:18]3[CH:19]=[N:20][CH:21]=[C:17]3[CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)([O:3]C)=[O:2].C[O-].[Na+].CO>O>[C:1]([C:5](=[CH2:22])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:18]3[CH:19]=[N:20][CH:21]=[C:17]3[CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 23321871HCID 23321871, compound

Product 1

HCID 13649429HCID 13649429, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 20 mg of 5-[p-(2-carbomethoxyprop-2-enyl)phenyl]imidazo[1,5-a]pyridine and 20 mg of sodium methoxide in 2 ml. of methanol is stirred under nitrogen for 1 hour at 25°. To the reaction mixture 2 ml. of water is added, and the homogenous solution is stirred at room temperature for 18 hours. The solvent is evaporated and the residue is redissolved in 5 ml of water and washed with 3 ml of ether. Acidification to pH=5, extraction with 10 ml of methylene chloride, drying over magnesium sulfate and evaporation yields 5-[p-(2-carboxyprop-2-enyl)phenyl]imidazo[1,5-a]pyridine, m.p. 171°-172°.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue is redissolved in 5 ml of water
  3. washwashed with 3 ml of ether
  4. extractionAcidification to pH=5, extraction with 10 ml of methylene chloride
  5. dry with materialdrying over magnesium sulfate and evaporation

Sources & evidence

ORD record
ord-2025e69e32f647c8951ccb51db2332cc
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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