(2-(5-Methylthiazol-2-yl)pyridin-4-yl)methanol → 2-(5-Methylthiazol-2-yl)isonicotinaldehyde

HRID 594296Notes

Reaction equation

HRID 594296 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][N:8]=2)=[N:4][CH:3]=1>ClCCCl.O=[Mn]=O>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[C:11]([CH:10]=[CH:9][N:8]=2)[CH:13]=[O:14])=[N:4][CH:3]=1

Participants

4

Reactant 1

HCID 69084104(2-(5-Methylthiazol-2-yl)pyridin-4-yl)methanol

Product 1

HCID 866956202-(5-Methylthiazol-2-yl)isonicotinaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A solution of (2-(5-methylthiazol-2-yl)pyridin-4-yl)methanol (1.910 g; 9.26 mmol) in anh. DCE (80 ml) was treated with MnO2 (4.025 g; 46.30 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-(5-methylthiazol-2-yl)isonicotinaldehyde as an off-white solid. LC-MS (conditions A): tR=0.65 min.; [M+H]+: 205.35 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-b54819fc474c4e8cace0e9fd001506fd
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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