Selenium Dioxide → 2-Phenylquinoline-7-carbaldehyde

HRID 1992420Notes

Reaction equation

HRID 1992420 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:9]2)=[CH:4][CH:3]=1.[Se](=O)=[O:19]>C(Cl)Cl>[C:12]1([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][C:2]([CH:1]=[O:19])=[CH:3][CH:4]=3)[N:9]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 2877157-Methyl-2-phenylquinoline

Product 1

HCID 468355462-Phenylquinoline-7-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 7-methyl-2-phenylquinoline (2.49 g, 11.4 mmol) and selenium dioxide (1.92 g, 17.3 mmol, 1.5 eq.) is heated to 160° C. (bath temp.) for 22 h. The cooled melt is suspended in CH2Cl2 with the aid of sonication and filtered through Celite and then through a plug of silica gel. This effectively removes the red color and the major lower spots. The material thus obtained is crystallized from hexanes/CHCl3, yielding a pale beige solid, mp. 108° C. The mother liquor is concentrated and chromatographed on silica gel [Jones Flashmaster, 50 g/150 mL cartridge, eluting with hexanes:CH2Cl2 1:1 (1-25)→1:3 (26-53)→CH2Cl2 (54-73)→3% EtOAc in CH2Cl2 (74-85)] to obtain the title compound as a pale yellow solid, mp. 109° C.; 1H NMR (CDCl3, 400 MHz) δ 7.48-7.60 (m, 3H), 7.94 (d, J=8.8 Hz, 1H), 8.01-8.05 (m, 2H), 8.18-8.23 (m, 2H), 8.29 (d, J=8.8 Hz, 1H), 8.64 (s, 1H), 10.26 (s, 1H) MS (ES+): m/z 234.2 (100) [MH+]; HPLC: tR=3.0 min (MicromassZQ, nonpolar—5 min).

Workup

  1. filtrationfiltered through Celite
  2. customThis effectively removes the red color
  3. customThe material thus obtained
  4. customis crystallized from hexanes/CHCl3
  5. customyielding a pale beige solid, mp. 108° C
  6. concentrationThe mother liquor is concentrated
  7. customchromatographed on silica gel [Jones Flashmaster, 50 g/150 mL cartridge
  8. washeluting with hexanes:CH2Cl2 1:1 (1-25)→1:3 (26-53)→CH2Cl2 (54-73)→3% EtOAc in CH2Cl2 (74-85)]

Sources & evidence

ORD record
ord-facb8d2e817a4d8797056450a474f1b5
Source dataset
uspto-grants-2010_01
Patent number
US07648987B2

Reaction notes

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