8-Methyl-2-o-tolylquinoline-3-carbaldehyde → 1-(8-Methyl-2-o-tolylquinolin-3-yl)ethanol

HRID 216752Notes

Reaction equation

HRID 216752 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[C:8]([CH:19]=[O:20])=[CH:7]2.[CH3:21][Mg]Cl>C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[C:8]([CH:19]([OH:20])[CH3:21])=[CH:7]2

Participants

4

Reactant 2

HCID 577078958-Methyl-2-o-tolylquinoline-3-carbaldehydeHCID 178418332HCID 178418332, compound

Product 1

HCID 577078131-(8-Methyl-2-o-tolylquinolin-3-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to Procedure K. To a mixture of 8-methyl-2-o-tolylquinoline-3-carbaldehyde (434 mg, 1.7 mmol) in THF (6 mL) at 0° C. was added dropwise a solution of MeMgCl (3M, 2 eq, 1.1 mL) and the reaction was stirred over night before quenched with NH4Cl saturated solution. The mixture was extracted with EtOAc (2×10 mL) and the combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: EtOAc/hexane, 1/1) to provide 1-(8-methyl-2-o-tolylquinolin-3-yl)ethanol as a white solid. 1H-NMR (CDCl3) δ 8.34 (s, 1H), 7.66 (d, J=8.2 Hz, 1H), 7.48 (d, J=6.7 Hz, 1H), 7.39 (t, J=7.8 Hz, 1H), 7.19-7.27 (m, 4H), 2.69 (s, 3H), 2.08 (s, 3H), 1.30 (m, 3H). Mass Spectrum (ESI) m/e=278 (M+1).

Workup

  1. customPrepared
  2. custombefore quenched with NH4Cl saturated solution
  3. extractionThe mixture was extracted with EtOAc (2×10 mL)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: EtOAc/hexane, 1/1)

Sources & evidence

ORD record
ord-42f3119a0a294b36803248c316eefb2d
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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