Hydrochloric Acid → 3-(2-aminoethyl)-2,3-dihydro-1H-indol-2-one hydrochloride
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH2:12])=[CH:2]1.CS(C)=[O:15].[ClH:17]>>[ClH:17].[NH2:12][CH2:11][CH2:10][CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]1=[O:15]Participants
4
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 2-(1H-indol-3-yl)ethanamine (6.00 g, 37.50 mmol) in DMSO (8.0 mL, 112.50 mmol) was added concentrated hydrochloric acid (9.5 mL, 112.50 mmol) slowly. The resulting reaction mixture was stirred at 50° C. in a sealed tube for 16 h. After cooling to room temperature, the reaction mixture was filtered. The resulting cake was stirred in EtOH (15 mL). The mixture was filtered and dried to give the desired title compound as a brown solid (5.00 g, 23.64 mmol, 63% yield). MS (ESI) m/z 177.2 [M+H]+.
Workup
- customThe resulting reaction mixture
- temperatureAfter cooling to room temperature
- filtrationthe reaction mixture was filtered
- stirringThe resulting cake was stirred in EtOH (15 mL)
- filtrationThe mixture was filtered
- customdried
Sources & evidence
- ORD record
- ord-24e71ac7b92141479d979681e2356368
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156798B2
Reaction notes
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