1-(2-Phenylquinolin-7-yl)-ethanol → 1-(2-Phenylquinolin-7-yl)-ethanone

HRID 230241Notes

Reaction equation

HRID 230241 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][C:11]([CH:17]([OH:19])[CH3:18])=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][C:11]([C:17](=[O:19])[CH3:18])=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 577623971-(2-Phenylquinolin-7-yl)-ethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 577623961-(2-Phenylquinolin-7-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into the CH2Cl2 (5 ml) solution of 1-(2-phenylquinolin-7-yl)-ethanol (236 mg, 0.947 mmol) was added PCC (408 mg, 2 eq.) under N2 at rt. After stirring for 18 h at rt, the reaction mixture was filtered through a silica pad and washed with EtOAc. After removing solvent, the title compound was obtained as brown oil. 1H NMR (CDCl3, 400 MHz): δ=2.78 (s, 3H), 7.48-7.58 (m, 3H), 7.87-7.89 (d, 1H, J=8.4 Hz), 7.96-7.98 (d, 1H, J=8.8 Hz), 8.09-8.12 (dd, 1H, J=1.6 & 8.4 Hz), 8.17-8.19 (m, 2H), 8.24-8.26 (d, 1H, J=8.8 Hz), 8.75 (s, 1H). MS (ES+): 248.3 [MH+]. HPLC: tR=3.6 min (MicromassZQ, polar—5 min).

Workup

  1. filtrationthe reaction mixture was filtered through a silica pad
  2. washwashed with EtOAc
  3. customAfter removing solvent

Sources & evidence

ORD record
ord-0ea3a4045e9d43a695945d817a33a1cc
Source dataset
uspto-grants-2009_07
Patent number
US07566721B2

Reaction notes

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