Ammonium Chloride → 1-[1-(1-Methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]ethanol

HRID 378377Notes

Reaction equation

HRID 378377 reaction equation
[CH3:1][Mg]Br.[CH3:4][CH:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([CH:17]=[O:18])=[CH:14][CH:15]=2)[CH2:10][CH2:9][CH2:8]1)[CH3:6].[Cl-].[NH4+]>CCOCC>[CH3:6][CH:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([CH:17]([OH:18])[CH3:1])=[CH:14][CH:15]=2)[CH2:10][CH2:9][CH2:8]1)[CH3:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 31574891-Isopropyl-1,2,3,4-tetrahydro-quinoline-6-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 106089181-[1-(1-Methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]ethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4.9 ml (15 mmol) of a 3.0M ethereal solution of methylmagnesium bromide was diluted with 15 ml of ether. An ethereal solution of 2.0 g (10 mmol) of 1-(1-methylethyl)-1,2,3,4-tetrahydroquinoline-6-carbaldehyde was dropped into the dilution prepared above at room temperature. The obtained mixture was stirred at room temperature for one hour, followed by the addition of an aqueous solution of ammonium chloride. The resulting mixture was extracted with thyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and concentrated in a vacuum to give 2.1 g of the title compound as a brown oil.

Workup

  1. customprepared above at room temperature
  2. extractionThe resulting mixture was extracted with thyl acetate
  3. washThe organic phase was washed with a saturated aqueous solution of common salt
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-5fd77841b5e0440790f62b049f953a51
Source dataset
uspto-grants-2000_02
Patent number
US06030964

Reaction notes

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