HCID 14296059, compound → 3,4-Dimethylpyridine-2-carbaldehyde

HRID 250967Notes

Reaction equation

HRID 250967 reaction equation
[CH3:1][C:2]1[C:3]([CH2:9][OH:10])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8]>O=[Mn]=O.C(Cl)Cl>[CH3:1][C:2]1[C:3]([CH:9]=[O:10])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 1

HCID 14296059HCID 14296059, compound

Product 1

HCID 214849533,4-Dimethylpyridine-2-carbaldehydeYield 80.3%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A CH2Cl2 solution (10 mL) of (3,4-dimethyl-pyridin-2-yl)-methanol (271 mg, 1.98 mmol) (Katz, R. B. et al. Synth. Commun. 1989, 19, 317-25) was treated with MnO2 (2.10 g, 21.8 mmol), and the resultant black suspension was stirred at room temperature overnight. The black suspension was filtered through a celite pad and the filtrate was concentrated in vacuo to afford 3,4-Dimethyl-pyridine-2-carbaldehyde (215 mg, 80%), without further purification, as a red oil. 1H NMR (CDCl3) δ 2.37 (s, 3H), 2.60 (s, 3H), 7.22-7.29 (m, 1H), 8.52 (d, 1H, J=4.3 Hz), 10.20 (s, 1H).

Workup

  1. filtrationThe black suspension was filtered through a celite pad
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3bf0cea0cdf14c85a2e37bfcd54ca7c6
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

Loading…