Diethyl Ether → HCID 14685746, compound

HRID 1088802Notes

Reaction equation

HRID 1088802 reaction equation
[CH:1]([N:3]([CH:7]1[C:16]2[C:11](=[C:12]([CH2:17][OH:18])[CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:19][CH3:20])[CH2:9][CH2:8]1)[CH:4]1[CH2:6][CH2:5]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].C(OCC)C>O1CCCC1>[CH3:1][N:3]([CH:7]1[C:16]2[C:11](=[C:12]([CH2:17][OH:18])[CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:19][CH3:20])[CH2:9][CH2:8]1)[CH:4]1[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 22161780HCID 22161780, compound

Product 1

HCID 14685746HCID 14685746, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(N-formyl-N-cyclopropylamino)-8-hydroxymethyl-1-ethyl-1,2,3,4-tetrahydroquinoline (0.34 g) in tetrahydrofuran (10 ml), lithium aluminum hydride (0.10 g) was added under ice-cooling and the mixture was refluxed gently for 1.5 hours. A saturated aqueous solution of Rochelle salt was added to the reaction mixture under ice-cooling, followed by addition of diethyl ether, the mixture was stirred for 1 hour at room temperature. After filtering off the precipitates, the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off to give 4-(N-methyl-N-cyclopropylamino)-8-hydroxymethyl-1-ethyl-1,2,3,4-tetrahydroquinoline (0.30 g).

Workup

  1. temperaturecooling
  2. temperaturethe mixture was refluxed gently for 1.5 hours
  3. temperaturecooling
  4. filtrationAfter filtering off the precipitates
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-ebd8227d372c438fb52d0867f43aa6f9
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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