Ammonium Chloride → 1-(7-Fluoroquinolin-6-yl)ethanol

HRID 456051Notes

Reaction equation

HRID 456051 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH:12]=[O:13].[CH3:14][Mg]Br.[NH4+].[Cl-]>C1COCC1>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH:12]([OH:13])[CH3:14]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 529829097-Fluoroquinoline-6-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 669272001-(7-Fluoroquinolin-6-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-fluoroquinoline-6-carbaldehyde (4.0 g, 22.84 mmol) in THF (30 ml) at 0° C., was added methylmagnesium bromide (2.85M in THF, 8 mL, 22.84 mmol) dropwise. The solution was stirred for 2 h, and NH4Cl was added to quench the reaction. The resulting mixture was extracted with EtOAc and the organic layer was washed with saturated NaHCO3 and NH4Cl, and dried over Na2SO4, filtered and concentrated to give the crude product, which was purified with Analogix gel silica using hexanes:EtOAc to afford 1-(7-fluoroquinolin-6-yl)ethanol (i). LCMS (method B): [MH]+=192, tR=1.84 min.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe resulting mixture was extracted with EtOAc
  4. washthe organic layer was washed with saturated NaHCO3 and NH4Cl
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product, which
  9. customwas purified with Analogix gel silica

Sources & evidence

ORD record
ord-47bc5633056e41208d5a4bc93d9706cc
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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