Dimethylformamide → 1-Methyl-2,3-dihydro-1H-indole
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:10](=O)([O-])[O-].[K+].[K+].CN(C)C=O.C(=O)(OC)OC>O>[CH3:10][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
Indoline (3 g, 0.025 mol), potassium carbonate (1.59), N,N-dimethylformamide (20 mL) and dimethyl carbonate (6.4 mL ,0.076 mol) were mixed together and heated to reflux (around 130 ° C.) for 14 h. The reaction, monitored by HPLC, went to completion within 14 h. The reaction mixture was cooled down to room temperature, then was slowly diluted with water (50 mL) and extracted with tert-butyl methyl ether (60 mL ). The organic extract was washed with water (3×50 mL) and the solution was evaporated to constant weight under reduced pressure to furnish 3.13 g of the product, N-methylindoline as a light yellow oil (95% yield).
Workup
- temperatureheated
- customThe reaction
- temperatureThe reaction mixture was cooled down to room temperature
- extractionextracted with tert-butyl methyl ether (60 mL )
- extractionThe organic extract
- washwas washed with water (3×50 mL)
- customthe solution was evaporated to constant weight under reduced pressure
Sources & evidence
- ORD record
- ord-3d943b30cb20422db91a3b65feb31b3a
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06326501B1
Reaction notes
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