Dimethylformamide → 1-benzyl-2,3-dihydroindole-5-carbaldehyde
Reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)[CH:19]=[O:20].P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:19]=[O:20])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Conditions
- Temperature
- 35 °C
Procedure
Into a 1,000 mλ reaction flask equipped with a thermometer, a stirrer, a condenser and a dropping funnel, 209 g (1.0 mol) of 1-benzylindoline and 365.5 g (5.0 mols) of N,N-dimethylformamide (DMF) were charged, and the temperature was raised to a liquid temperature of from 30 to 40° C. Then, while stirring at the same temperature, 161.0 g (1.05 mols) of phosphorus oxychloride was dropwise added thereto over a period of about two hours from the dropping funnel. After completion of the dropwise addition, stirring was continued for three hours at from 80 to 100° C. After completion of the reaction, the reaction solution was cooled to room temperature and put into 1 kg of ice water. At a temperature of from 30 to 40° C., a 24% sodium hydroxide aqueous solution was dropwise added thereto to bring the liquid alkaline, whereby the precipitated solid was collected by filtration, washed with water and dried to obtain 230.2 g (yield: 97%) of 1-benzyl-5-formylindoline as a slightly yellow powder.
Workup
- customInto a 1,000 mλ reaction flask
- additionwere charged
- additionwas dropwise added
- additionAfter completion of the dropwise addition
- waitwas continued for three hours at from 80 to 100° C
- customAfter completion of the reaction
- temperaturethe reaction solution was cooled to room temperature
- filtrationwas collected by filtration
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-8cdebfb63b45487fb656b36d14763335
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06066744
Reaction notes
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