Aluminium lithium hydride → (1-Isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)amine
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[N:8]([CH:13]([CH3:15])[CH3:14])[C:7](=O)[CH2:6][C:5]2([CH3:18])[CH3:17].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:13]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([NH2:1])=[C:11]([CH3:12])[CH:10]=2)[C:5]([CH3:18])([CH3:17])[CH2:6][CH2:7]1)([CH3:15])[CH3:14]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
6-Amino-1-isopropyl-4,4,7-trimethyl-2-oxo-1,2,3,4-tetrahydroquinoline (12) (0.78 g, 3.2 mmol) was dissolved in tetrahydrofuran (50 mL) and the solution was cooled to 0° C. under argon. The solution was treated with 1M lithium aluminum hydride (4.0 mL, 4.0 mmol) and the reaction stirred at 0° C. to room temperature for 24 hours. The reaction mixture was cooled to 0° C., poured onto ice and extracted with ether (2×). The combined organic extracts were washed with brine and dried (MgSO4). The filtered solution was concentrated under reduced pressure and the crude product was purified by silica gel chromatography (5% ethyl acetate in hexanes) to give the title compound (0.87 g, >100%) as an oil.
Workup
- temperatureThe reaction mixture was cooled to 0° C.
- additionpoured onto ice
- extractionextracted with ether (2×)
- washThe combined organic extracts were washed with brine
- dry with materialdried (MgSO4)
- concentrationThe filtered solution was concentrated under reduced pressure
- customthe crude product was purified by silica gel chromatography (5% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-afca615b12c84c36bacf6840338c0e97
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06127382
Reaction notes
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