Ammonium Chloride → 1-(2-Phenylquinolin-7-yl)-ethanol

HRID 230242Notes

Reaction equation

HRID 230242 reaction equation
[CH3:1][Mg+].[Br-].[C:4]1([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][C:14]([CH:20]=[O:21])=[CH:15][CH:16]=3)[N:11]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH4+].[Cl-]>C1COCC1>[C:4]1([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][C:14]([CH:20]([OH:21])[CH3:1])=[CH:15][CH:16]=3)[N:11]=2)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 468355462-Phenylquinoline-7-carbaldehydeHCID 178418689HCID 178418689, compound

Product 1

HCID 577623971-(2-Phenylquinolin-7-yl)-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into the THF (50 ml) solution of MeMgBr (3M in Et2O, 5.6 mL, 1.5 eq.) was added dropwise the THF (40 ml) solution of 2-phenylquinoline-7-carbaldehyde (2625 mg, 11.25 mmol) under N2 at rt over 20 min. After stirring at rt for 3 h, the reaction mixture was treated with saturated aqueous NH4Cl solution (100 ml), and the organic phase was separated. The aqueous phase was extracted with EtOAc (2×100 ml). The combined organic phases were then washed with H2O (2×100 ml) and brine (100 ml), dried over MgSO4, filtered and concentrated to give the title compound as brown oil. The crude material was used for the next step without further purification. 1H NMR (CDCl3, 400 MHz): δ=1.60-1.62 (d, 3H, J=6.4 Hz), 2.08 (brs, 1H), 5.11-5.14 (m, 1H), 7.44-7.60 (m, 4H), 7.81-7.83 (d, 1H, J=8.4 Hz), 7.85-7.87 (d, 1H, J=8.4 Hz), 8.13-8.17 (m, 3H), 8.19-8.21 (d, 1H, J=8.4 Hz). MS (ES+): 250.3 [MH+]. HPLC: tR=2.9 min (MicromassZQ, polar—5 min).

Workup

  1. customthe organic phase was separated
  2. extractionThe aqueous phase was extracted with EtOAc (2×100 ml)
  3. washThe combined organic phases were then washed with H2O (2×100 ml) and brine (100 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-255d454a516745e7bff7c699d45f2129
Source dataset
uspto-grants-2009_07
Patent number
US07566721B2

Reaction notes

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