[2-Fluoro-5-(6-isopropyl-quinolin-8-yl)-phenyl]-methanol → 2-Fluoro-5-(6-isopropylquinolin-8-yl)-benzaldehyde

HRID 896700Notes

Reaction equation

HRID 896700 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:18]([CH3:20])[CH3:19])[CH:11]=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)=[CH:4][C:3]=1[CH2:21][OH:22]>C(Cl)Cl.O=[Mn]=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:18]([CH3:20])[CH3:19])[CH:11]=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)=[CH:4][C:3]=1[CH:21]=[O:22]

Participants

4

Reactant 1

HCID 22350104[2-Fluoro-5-(6-isopropyl-quinolin-8-yl)-phenyl]-methanol

Product 1

HCID 223500542-Fluoro-5-(6-isopropylquinolin-8-yl)-benzaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of [2-fluoro-5-(6-isopropyl-quinolin-8-yl)-phenyl]-methanol from Step 2 (2.23 g, 7.55 mmol) and MnO2 (13 g, 150 mmol) in CH2Cl2 (70 mL) was stirred at 21° C. for 18 h. The mixture was filtered through a pad of celite and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 70:30) provided the 2-fluoro-5-(6-isopropylquinolin-8-yl)-benzaldehyde compound.

Workup

  1. filtrationThe mixture was filtered through a pad of celite and
  2. concentrationconcentrated
  3. customPurification
  4. washby flash chromatography (eluting with hexane/ethyl acetate, 70:30)

Sources & evidence

ORD record
ord-396d1c92f0a344da88be10e31e1bae29
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

Loading…