1,2,3,4-Tetrahydro-1-nitrosoquinoline → 1,2,3,4-Tetrahydroquinolin-1-amine
Reaction equation
[N:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:3]1([NH2:1])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 1-nitroso-1,2,3,4-tetrahydroquinoline (10.0 g, 61.66 mmol) in 60 mL dry THF was added dropwise to a refluxing suspension of LiAlH4 (4.26 g, 112.21 mmol) in 130 mL THF. The reaction was allowed to reflux for 1 hour, cooled to 0° C., and then quenched by the dropwise addition of Rochelle's salt solution. The resulting precipitate was diluted with THF and filtered. The filtrate was then concentrated under reduced pressure, then purified by flash chromatography to give the product (4.83 g, 52.9%) as a white solid. 1H-NMR (300 MHz, CDCl3): δ 7.12 (m, 2H), 6.95 (d, 1H), 6.69 (m, 1H), 3.32 (m, 2H), 2.75 (t, 2H), 2.04 (dt, 2H) ppm; MS m/z calculated for C9H13NO (M+H): 149.1. Found 149.1 (M+H, ESI+).
Workup
- temperatureto reflux for 1 hour
- customquenched by the dropwise addition of Rochelle's salt solution
- additionThe resulting precipitate was diluted with THF
- filtrationfiltered
- concentrationThe filtrate was then concentrated under reduced pressure
- custompurified by flash chromatography
Sources & evidence
- ORD record
- ord-34f28db9c07f49e380c2b0a845fb04c5
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08309059B2
Reaction notes
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