2-Chloro-7-fluoroquinoline-3-carbaldehyde → 1-(2-Chloro-7-fluoroquinolin-3-yl)ethanol

HRID 216781Notes

Reaction equation

HRID 216781 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=1.[CH3:15][Mg+].[Br-]>C1COCC1>[Cl:1][C:2]1[C:11]([CH:12]([OH:13])[CH3:15])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 120991792-Chloro-7-fluoroquinoline-3-carbaldehydeHCID 178418689HCID 178418689, compound

Product 1

HCID 242760771-(2-Chloro-7-fluoroquinolin-3-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-chloro-7-fluoroquinoline-3-carbaldehyde (44.7 g, 213 mmol) in THF (600 mL) was treated with MeMgBr (78 mL, 1.1 eq) dropwise at −20° C. After overnight, the reaction was quenched with NH4Cl solution and extracted with Ether (300 mL and 100 mL). The organics were washed with water, brine, dried over Na2SO4, concentrated and recrystallized from EtOAc (100 mL) and hexane (1 L). A pale yellow solid was obtained (41 g, 85%). 1H NMR (400 MHz, CDCl3) δ ppm 8.41 (s, 1H), 7.87 (dd, J=8.0, 4.0 Hz, 1H), 7.67 (dd, J=8.0, 2.0 Hz, 1H), 7.38 (td, J=8.0, 2.0 Hz, 1H), 5.38 (q, J=4.0 Hz, 1H), 1.63 (d, J=4.0 Hz, 3H). Mass Spectrum (ESI) m/e=226 (M+1).

Workup

  1. customthe reaction was quenched with NH4Cl solution
  2. extractionextracted with Ether (300 mL and 100 mL)
  3. washThe organics were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customrecrystallized from EtOAc (100 mL) and hexane (1 L)
  7. customA pale yellow solid was obtained (41 g, 85%)

Sources & evidence

ORD record
ord-40b20611a1934519af3b3252914a7eb3
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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