Methanol → HCID 13821855, compound

HRID 649161Notes

Reaction equation

HRID 649161 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-8debca15b127476d8b1c0b26bb74b6e9
Source dataset
uspto-grants-1988_04
Patent number
US04738967

Reaction notes

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