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

HRID 2229167Notes

Reaction equation

HRID 2229167 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 ethyl 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 ethyl 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-2cdbacd29c21476aa6789a4bd5b15cb3
Source dataset
uspto-grants-2002_07
Patent number
US06420363B1

Reaction notes

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