Dimethylformamide → 1-Isopropyl-1,2,3,4-tetrahydro-quinoline-6-carbaldehyde
Reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[CH3:11][CH:12]([N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH2:15]1)[CH3:13].C(=O)([O-])O.[Na+]>>[CH3:13][CH:12]([N:14]1[C:23]2[C:18](=[CH:19][C:20]([CH:8]=[O:9])=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH2:15]1)[CH3:11]Participants
Procedure
18.6 g (0.12 mol) of phosphorus oxychloride was dropped into 29.2 g (0.4 mol) of N,N-dimethylformamide under cooling with ice. The obtained mixture was stirred at room temperature for 30 minutes and cooled again on an ice bath. 17.5 g (0.1 mol) of 1-(1-methylethyl)-1,2,3,4-tetrahydroquinoline was gradually dropped into the resulting mixture. The mixture thus obtained was stirred at room temperature for one hour and poured onto ice-water. The resulting mixture was neutralized with an aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and concentrated in a vacuum. The residue was purified by silica gel column chromatography (10% ethyl acetate/n-hexane) to give 11.4 g of the title compound as a reddish-brown oil.
Workup
- temperatureunder cooling with ice
- temperaturecooled again on an ice bath
- customThe mixture thus obtained
- stirringwas stirred at room temperature for one hour
- additionpoured onto ice-water
- extractionextracted with ethyl acetate
- dry with materialThe organic phase was dried over anhydrous magnesium sulfate
- concentrationconcentrated in a vacuum
- customThe residue was purified by silica gel column chromatography (10% ethyl acetate/n-hexane)
Sources & evidence
- ORD record
- ord-c8be8705666c42e99478d0250f6aa101
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06291508B1
Reaction notes
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