Propargyl alcohol → 7-Chloro-2-methyl-3-propargyloxymethylimidazo[2,1-a]isoquinoline
Reaction equation
[H-].[Na+].[I-].[Cl:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][N:9]1[C:17]([CH2:18][N+](C)(C)C)=[C:16]([CH3:23])[N:15]=[C:10]12.[CH2:24]([OH:27])[C:25]#[CH:26]>>[Cl:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][N:9]1[C:17]([CH2:18][O:27][CH2:24][C:25]#[CH:26])=[C:16]([CH3:23])[N:15]=[C:10]12Participants
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 60% sodium hydride (0.235 g) in propargyl alcohol (9.36 ml) was added 7-chloro-2-methyl-3-trimethylammoniomethylimidazo[2,1-a]isoquinoline iodide (2.08 g) and the mixture was heated at 100° C. with stirring for 2 hours. After being cooled, the mixture was evaporated in vacuo and the residue was dissolved in chloroform. The solution was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (20 g) with a mixture of chloroform and methanol (100:1) as an eluent to give 7-chloro-2-methyl-3-propargyloxymethylimidazo[2,1-a]isoquinoline. This compound was treated with a solution of hydrogen chloride in ethanol to give 7-chloro-2-methyl-3-propargyloxymethylimidazo[2,1-a]isoquinoline hydrochloride (1 g).
Workup
- temperatureAfter being cooled
- customthe mixture was evaporated in vacuo
- dissolutionthe residue was dissolved in chloroform
- washThe solution was washed with water
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
- customThe residue was purified by column chromatography on silica gel (20 g) with a mixture of chloroform and methanol (100:1) as an eluent
Sources & evidence
- ORD record
- ord-fbb52a3eca9e49a7bbf71580fb91e71d
- Source dataset
- uspto-grants-1988_04
- Patent number
- US04738967
Reaction notes
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