Indole → 2-(1-methyl-1H-indol-3-yl)acetonitrile
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]#[N:12])=[CH:2]1.[C:13](=O)([O-])[O-].[K+].[K+].C(=O)(OC)OC.N1C2C(=CC=CC=2)C=C1>O.CN(C)C=O>[CH3:13][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]#[N:12])=[CH:2]1Participants
Conditions
- Temperature
- 124 °C
Procedure
A 500 mL, three-necked flask equipped with a thermocouple, condenser, and addition funnel was charged with indole-3-acetonitrile (10.0 g, 0.064 mol), potassium carbonate (5.0 g, 36 mmol), N,N-dimethylformamide (60 mL) and dimethyl carbonate (11.0 mL, 0.13 mol). The resulting mixture was heated to 124±1° C. The progress of the reaction was monitored by HPLC. After 10 h at this temperature, the presence of the starting indole could not be detected. The reaction mixture was then cooled to zero to −5° C. Water (140 mL) was added which resulted in the formation of a precipitate. The mixture was stirred at −5° C. for 1 hour, then the solid was collected by filtration, washed with water (150 mL), and dried under high vacuum at 45° C. for 24 h to give 1-methylindole-3-acetonitrile (I and II, 9.69 g, 89%) as a brown solid.
Workup
- customA 500 mL, three-necked flask equipped with a thermocouple, condenser, and addition funnel
- temperatureThe reaction mixture was then cooled to zero to −5° C
- customresulted in the formation of a precipitate
- filtrationthe solid was collected by filtration
- washwashed with water (150 mL)
- customdried under high vacuum at 45° C. for 24 h
Sources & evidence
- ORD record
- ord-11de2212ca74433cb9b1867e5b4fbd25
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06326501B1
Reaction notes
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