Methanol → methyl 1-methyl-1H-indole-7-carboxylate
Reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([OH:13])=[O:12])[CH:4]=[CH:3]1.S(Cl)(Cl)=O.[CH3:18]O>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([O:13][CH3:18])=[O:12])[CH:4]=[CH:3]1Participants
4
Procedure
To 70 ml of a methanol solution of 1.82 g (10.4 mmol) of 1-methyl-7-indolecarboxylic acid was added dropwise 3.09 g (26.0 mmol) of thionyl chloride at 0° C. The reaction mixture was refluxed for 2 hours and the solvent was then distilled off under reduced pressure. Ice water was poured onto the resulting residue and ammonium hydroxide was added to render the mixture alkaline. The mixture was extracted three times with ethyl acetate. The combined extracts were washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was isolated and purified by silica gel column chromatography to give 1.16 g (59.0%) of methyl 1-methyl-7-indolecarboxylate.
Workup
- temperatureThe reaction mixture was refluxed for 2 hours
- distillationthe solvent was then distilled off under reduced pressure
- additionIce water was poured onto the resulting residue and ammonium hydroxide
- additionwas added to render the mixture alkaline
- extractionThe mixture was extracted three times with ethyl acetate
- washThe combined extracts were washed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was then distilled off under reduced pressure
- customThe residue was isolated
- custompurified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-fc9e6568bc884a6cab5f2fa22de64893
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06169107A
Reaction notes
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