Dimethylformamide → 3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acid
Reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[NH:11]1[C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[C:13]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:12]1.[OH-].[Na+]>O.ClCCl>[CH:3]([C:12]1[NH:11][C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[C:13]=1[CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -9 °C
Procedure
A mixture of 24 g of dimethylformamide and 300 mL of dichloromethane was cooled to −9° C. Phosphorus oxychloride (50 g) was rapidly added via an addition funnel. 3-(4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid (54.9 g) was added in portions with vigorous stirring. The mixture was warmed to room temperature and then refluxed for 10 minutes. It was then cooled to 5° C. and diluted with 300 mL of water. The pH was adjusted to 10 using 10N sodium hydroxide. The layers were separated. The aqueous layer was cooled to 10° C. and the pH adjusted to 2-3 with about 130 mL of 10 N hydrochloric acid. The oil which formed solidified and was collected by vacuum filtration, washed three times with water and dried under vacuum at 50° C. to give 52.8 g (93% yield) of 3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid as a dark brown solid.
Workup
- temperatureThe mixture was warmed to room temperature
- temperaturerefluxed for 10 minutes
- temperatureIt was then cooled to 5° C.
- customThe layers were separated
- temperatureThe aqueous layer was cooled to 10° C.
- customThe oil which formed
- filtrationwas collected by vacuum filtration
- washwashed three times with water
- customdried under vacuum at 50° C.
Sources & evidence
- ORD record
- ord-a9b6408df0e14460820b2b1dcc793de5
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06855730B2
Reaction notes
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