Water → 6-[4-(Trifluoromethyl)phenyl]-1,2,3,4-tetrahydroquinoline

HRID 1842029Notes

Reaction equation

HRID 1842029 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=O)[CH2:13][CH2:12]3)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[F:21][C:2]([F:1])([F:20])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH2:14][CH2:13][CH2:12]3)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 120009366-(4-(trifluoromethyl)phenyl)-3,4-dihydroquinolin-2(1H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 120011176-[4-(Trifluoromethyl)phenyl]-1,2,3,4-tetrahydroquinolineYield 80.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

630 mg 6-(4-Trifluoromethyl-phenyl)-3,4-dihydro-1H-quinolin-2-one were dissolved in 10 ml tetrahydrofuran. 4.76 ml lithium aluminiumhydride 1M solution in tetrahydrofuran were added and the reaction mixture stirred for one hour at room temperature. Then 100 μl water and 100 μl 15% sodium hydroxide solution were added to the ice cooled reaction mixture. Then the reaction mixture was filtered off insoluble salts, and the filtrate evaporated under reduced pressure to obtain 485 mg 6-(4-Trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-quinoline.

Workup

  1. temperaturecooled
  2. customreaction mixture
  3. filtrationThen the reaction mixture was filtered off insoluble salts
  4. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-b9e80d4a57374fd08a7b892ea7f1a970
Source dataset
uspto-grants-2015_02
Patent number
US08946212B2

Reaction notes

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