Ammonium Chloride → 1-(Quinolin-2-yl)ethanol

HRID 1741778Notes

Reaction equation

HRID 1741778 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[O:12].[CH3:13][Mg]Br.[NH4+].[Cl-]>C1COCC1.C1(C)C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([OH:12])[CH3:13]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 796192-QuinolinecarboxaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 122102981-(Quinolin-2-yl)ethanol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold (0° C.) solution of quinoline-2-carboxaldehyde (7.85 g) in THF (100 mL) was added dropwise 1.4M methyl magnesium bromide in toluene and THF (46 mL). After total addition, the mixture was stirred at room temperature for 30 min. The reaction mixture was poured into aqueous satured NH4Cl (500 mL), extracted with ethyl acetate (2×200 mL), washed with brine (100 mL), and dried (MgSO4). The solution was evaporated to dryness and chromatographed on flash silica gel using ethyl acetate:hexane (3:7) as eluant to yield the title product as a light orange solid.

Workup

  1. additionAfter total addition
  2. extractionextracted with ethyl acetate (2×200 mL)
  3. washwashed with brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. customThe solution was evaporated to dryness
  6. customchromatographed on flash silica gel

Sources & evidence

ORD record
ord-0e10d7d1cfe14b7c9411277eea4db77b
Source dataset
uspto-grants-1994_08
Patent number
US05334719

Reaction notes

Loading…