Methanol → HCID 13821855, compound

HRID 1788935Notes

Reaction equation

HRID 1788935 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]1[C:16]([CH2:17][C:18]([O:20]CC)=[O:19])=[C:15]([CH3:23])[N:14]=[C:9]12.CO>O>[C:18]([CH2:17][C:16]1[N:8]2[CH:7]=[CH:6][C:5]3[C:10]([C:9]2=[N:14][C:15]=1[CH3:23])=[CH:11][CH:12]=[CH:13][C:4]=3[Cl:3])([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 13821854HCID 13821854, compound

Product 1

HCID 13821855HCID 13821855, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (1.25 g) in water (5 ml) was added to a mixture of 7-chloro-3-ethoxycarbonylmethyl-2-methylimidazo[2,1-a]isoquinoline (4.75 g) and methanol (48 ml) and the mixture was refluxed for 1.5 hours. After being cooled, the mixture was evaporated in vacuo and 1N hydrochloric acid (31.4 ml) was added to the residue under ice-cooling. The resulting precipitate was collected by filtration, washed with water, dried in a desiccator and washed with a mixture of ethanol and methanol to give 3-carboxymethyl-7-chloro-2-methylimidazo[2,1-a]isoquinoline (3.2 g).

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. temperatureAfter being cooled
  3. customthe mixture was evaporated in vacuo and 1N hydrochloric acid (31.4 ml)
  4. additionwas added to the residue under ice-
  5. temperaturecooling
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water
  8. customdried in a desiccator
  9. washwashed with a mixture of ethanol and methanol

Sources & evidence

ORD record
ord-8d9ad75ce0ee48ae823f1d493e44156c
Source dataset
uspto-grants-1987_08
Patent number
US04686227

Reaction notes

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