(2-Phenylquinolin-7-yl)methanol → 7-Methyl-2-phenylquinoline

HRID 386159Notes

Reaction equation

HRID 386159 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][C:11]([CH:17]=O)=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C2C=CC3C(=CC(CO)=CC=3)N=2)C=CC=CC=1>C(Cl)(Cl)Cl.O=[Mn]=O>[CH3:17][C:11]1[CH:10]=[C:9]2[C:14]([CH:15]=[CH:16][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8]2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 22062823(2-Phenylquinolin-7-yl)methanolHCID 468355462-Phenylquinoline-7-carbaldehyde

Product 1

HCID 2877157-Methyl-2-phenylquinoline

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

Additionally, 2-phenylquinoline-7-carbaldehyde could be prepared as follows: To a solution of (2-phenylquinolin-7-yl)methanol (75 mg, 0.319 mmol) in chloroform (1 mL) was added MnO2 (277 mg, 3.19 mmol). The mixture was stirred at it for 20 h and filtered through a Celite pad. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography. (1% MeOH in dichloromethane) to afford the title compound. 1H-NMR (CDCl3, 400 MHz) δ 7.50-7.59 (m, 3 H), 7.95 (d, J=8.8 Hz, 1 H), 8.04 (dd, J=2.4, 8.8 Hz, 2 H), 8.19-8.22 (m, 2 H), 8.31 (d, J=8.8 Hz, 1 H), 8.69 (s, 1 H), 10.26 (s, 1 H). MS (ES+): m/z 234 [MH+]. HPLC: tR=3.59 min (OpenLynx, polar—5 min).

Workup

  1. filtrationfiltered through a Celite pad
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-23195376ecde43c9bd13d3dc6901a629
Source dataset
uspto-grants-2013_02
Patent number
US08367826B2

Reaction notes

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