Chloroacetamide → Methyl 7-carbamoylmethoxy-1-methyl-2-indolecarboxylate
Reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7]2.[H-].[Na+].Cl[CH2:19][C:20]([NH2:22])=[O:21]>CN(C)C=O>[C:20]([CH2:19][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7]2)(=[O:21])[NH2:22]Participants
Procedure
After 0.50 g (2.44 mmol) of methyl 7-hydroxy-1-methyl-2-indolecarboxylate was added to a suspension of 0.01 g (2.44 mmol) of 60% sodium hydride in 25 ml of dimethyl-formamide, the mixture was stirred at room temperature until the mixture became a transparent solution. Then 0.25 g (2.68 mmols) of 2-chloroacetamide was added dropwise to the transparent solution at room temperature followed by stirring at 50° C. for an hour. The reaction mixture was poured onto ice water. The resulting mixture was then extracted three times with ethyl acetate. The combined extracts were washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 0.54 g (84.4%) of methyl 7-carbamoylmethoxy-1-methyl-2-indolecarboxylate.
Workup
- stirringby stirring at 50° C. for an hour
- additionThe reaction mixture was poured onto ice water
- extractionThe resulting mixture was then extracted three times with ethyl acetate
- washThe combined extracts were washed with water
- dry with materialAfter drying over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-bb91b637e931465c970104e95c24bc0e
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06169107A
Reaction notes
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