(2-(4-Methylthiazol-2-yl)pyridin-4-yl)methanol → 2-(4-Methylthiazol-2-yl)isonicotinaldehyde

HRID 594293Notes

Reaction equation

HRID 594293 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:7]2[CH:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][N:8]=2)[S:5][CH:6]=1>ClCCCl.O=[Mn]=O>[CH3:1][C:2]1[N:3]=[C:4]([C:7]2[CH:12]=[C:11]([CH:10]=[CH:9][N:8]=2)[CH:13]=[O:14])[S:5][CH:6]=1

Participants

4

Reactant 1

HCID 69083230(2-(4-Methylthiazol-2-yl)pyridin-4-yl)methanol

Product 1

HCID 866956192-(4-Methylthiazol-2-yl)isonicotinaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A solution of (2-(4-methylthiazol-2-yl)pyridin-4-yl)methanol (750 mg; 3.64 mmol) in anh. DCE (40 ml) was treated with MnO2 (1.581 g; 18.20 mmol), and the resulting mixture was heated at reflux, under nitrogen, for 1.5 h. After cooling to rt, the resulting reaction mixture was filtered over celite, and the separated solids were washed with DCM. The filtrate was concentrated to dryness under reduced pressure giving 2-(4-methylthiazol-2-yl)isonicotinaldehyde as an off-white solid. LC-MS (conditions A): tR=0.64 min.; [M+H]+: 205.04 g/mol.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux, under nitrogen, for 1.5 h
  3. customthe resulting reaction mixture
  4. filtrationwas filtered over celite
  5. washthe separated solids were washed with DCM
  6. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-984b2cad35f944ea8766820f9c0eb8f0
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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