Ethyl Acetate → 3-(N-Propyl)amino-1,2,3,4-tetrahydroquinoline

HRID 266170Notes

Reaction equation

HRID 266170 reaction equation
[C:1]([NH:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH2:7]1)(=O)[CH2:2][CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[OH-].[Na+]>C(OCC)C.O1CCCC1.O>[CH2:1]([NH:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH2:7]1)[CH2:2][CH3:3]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 196976643-(N-Propionyl)amino-1,2,3,4-tetrahydroquinolineHCID 21226445Aluminium lithium hydride

Product 1

HCID 220340883-(N-Propyl)amino-1,2,3,4-tetrahydroquinolineYield 89.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a ice-cooled solution of 3.2 g (15.6 mmol) 3-(N-propionyl)amino-1,2,3,4-tetrahydroquinoline in 50 ml dry diethyl ether and 80 ml dry tetrahydrofurane was 3.0 g (79 mmol) lithium aluminum hydride added. The mixture was gently heated to reflux and kept that way for 5 days. Ethyl acetate (4.5 ml), 3.0 ml water,3.0 ml 15% sodium hydroxide and 9 ml water was added consecutively. The precipitate appearing after 5 minutes was filtered off and washed with diethyl ether. Evaporation of the etheric solution yielded 2.66 g (89%) of the desired product: 13C NMR 0 d 11 (76), 23.46, 33.71, 46.41, 48.98, 50.43, 113.79, 117.29, 119.37, 126.87, 130.06, 144.09; MS m/e 190 (M+, 17), 132 (100), 130 (32), 72 (22), 118 (17), 131 (17).

Workup

  1. additionadded
  2. temperatureThe mixture was gently heated
  3. temperatureto reflux
  4. customfor 5 days
  5. filtrationwas filtered off
  6. washwashed with diethyl ether
  7. customEvaporation of the etheric solution

Sources & evidence

ORD record
ord-d9adab24ec0b42f1bbc9d665c2403ead
Source dataset
uspto-grants-1997_07
Patent number
US05650427

Reaction notes

Loading…