HCID 67272592, compound → 3-Methyl-5-(trifluoromethyl)pyridine-2-carbaldehyde

HRID 1592386Notes

Reaction equation

HRID 1592386 reaction equation
C[C:2]1([CH2:13][OH:14])[C:7]([CH3:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][NH:3]1>C(Cl)Cl.O=[Mn]=O>[CH3:8][C:7]1[C:2]([CH:13]=[O:14])=[N:3][CH:4]=[C:5]([C:9]([F:12])([F:10])[F:11])[CH:6]=1

Participants

4

Reactant 1

HCID 67272592HCID 67272592, compound

Product 1

HCID 716270703-Methyl-5-(trifluoromethyl)pyridine-2-carbaldehydeYield 61%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of (2,3-dimethyl-5-trifluoromethyl-pyridin-2-yl)-methanol (0.300 g, 1.57 mmol)) and activated MnO2 (1.36 g, 15.6 mmol) in CH2Cl2 (10 mL) was stirred at room temperature overnight. After that period of time the suspension was filtered through a celite cake. the solvent was removed from the filtrate, and the residue was purified on silica gel column (CH2Cl2) to afford 3-methyl-5-trifluoromethyl-pyridine-2-carbaldehyde as a pale yellow liquid (0.180 g, 61%). 1H NMR (CD3Cl) δ 2.73 (s, 3H), 7.87 (s, 1H), 8.90 (s, 1H), 10.23 (s, 1H). 2.49 (s, 6H), 2.89-2.94 (m, 4H), 4.51 (s, 2H), 4.55 (s, 2H), 7.84 (dd, 1H, J=5.7, 8.1 Hz), 8.34 (d, 1H, J=8.1 Hz), 8.53 (s, 1H), 8.60 (d, 1H, J=5.7 Hz), 8.94 (s, 1H); 13C NMR (D2O) δ 17.48, 17.65, 22.50, 24.82, 39.49, 54.45, 55.28, 55.42, 126.63, 137.69, 138.39, 138.48, 139.41, 143.21, 143.25 148.63, 148.74, 154.80; 19F NMR (D2O) δ 13.32. ES-MS m/z 367 (M+H). Anal. Calcd. for C19H25F3N4.4.4HBr.3.5H2O.0.9C4H10O: C, 31.85; H, 5.37; N, 6.57; Br, 41.26. Found: C, 31.85; H, 5.13; N, 6.55; Br, 41.18.

Workup

  1. filtrationAfter that period of time the suspension was filtered through a celite cake
  2. customthe solvent was removed from the filtrate
  3. customthe residue was purified on silica gel column (CH2Cl2)

Sources & evidence

ORD record
ord-a0379ce409c7484c9826bd9f6fd65e14
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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