Sodium Hydroxide → 1-(2-(Dimethylamino)ethyl)-1,2,3,4-tetrahydroquinolin-6-amine

HRID 1922366Notes

Reaction equation

HRID 1922366 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])[C:7](=O)[CH2:6][CH2:5]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:15][N:14]([CH3:16])[CH2:13][CH2:12][N:8]1[C:9]2[C:4](=[CH:3][C:2]([NH2:1])=[CH:11][CH:10]=2)[CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 43446585HCID 43446585, compound

Product 1

HCID 284190641-(2-(Dimethylamino)ethyl)-1,2,3,4-tetrahydroquinolin-6-amineYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-amino-1-(2-(dimethylamino)ethyl)-3,4-dihydroquinolin-2(1H)-one (1.3 g, 5.57 mmol) in 10 mL anhydrous THF was added dropwise to a cooled suspension of 1M LiAlH4 in THF (22.3 mL, 22.3 mmol). The suspension was stirred at room temperature for 1 day. After this time, the mixture was cooled to 0° C. and treated with 5 mL 1N NaOH dropwise with rapid stirring. After stirring for 30 minutes, the suspension was treated with Na2SO4 and filtered. The filter cake was rinsed with 10% 2M NH3 in MeOH/CH2Cl2 (100 mL total). The filtrate was concentrated and the dark residue was subjected to flash chromatography on silica gel using 5-10% 2M NH3 in MeOH/CH2Cl2 to give a dark viscous oil (930 mg, 76.2%). 1H-NMR (CDCl3) δ: 6.49 (brs, 2H), 6.40 (s, 1H), 3.34-3.30 (m, 2H), 3.30 (br s, 2H), 3.21 (t, J=5.7 Hz, 2H), 2.68 (t, J=5.7 Hz, 2H), 2.49-2.44 (m, 2H), 2.28 (s, 6H), 1.95-1.87 (m, 2H).

Workup

  1. temperatureAfter this time, the mixture was cooled to 0° C.
  2. stirringAfter stirring for 30 minutes
  3. filtrationfiltered
  4. washThe filter cake was rinsed with 10% 2M NH3 in MeOH/CH2Cl2 (100 mL total)
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4c33195b3a7e41df8a02f16bdf1dbbb9
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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