Ammonium Persulfate → (4-Chloropyridin-2-yl)methanol

A solution of 4-chloropyridine N-oxide (5 g, 38.6 mmol) and trimethyloxonium tetrafluoroborate (5.94 g, 40.1 mmol) in CH2Cl2 (115 mL) was stirred for two hours at ambient temperature. The solvent was evaporated and the residue taken up in MeOH (115 mL) and heated to near boiling. Ammonium persulfate (1.76 g, 7.72 mmol) dissolved in H2O (7.7 mL) was added and the mixture was heated to reflux for 30 min. A second portion of ammonium persulfate (0.88 g) in H2O (3.9 mL) was added and the mixture was refluxed for another 30 min. The solvent was evaporated and the residue was partitioned between CH2Cl2 and aqueous Na2CO3 (10% w/v). The organic layer was washed with H2O, dried over MgSO4, and evaporated leaving 2.4 g (43%) of the title compound. 1H NMR (CDCl3) δ 8.20 (d, 1H, J=5.0 Hz, H-6); 7.31 (s, 1H, H-3); 7.04 (d, 1H, J=5.0 Hz, H-5); 5.46 (s, 1H, OH); 4.61 (s, 2H, CH2).

1. customThe solvent was evaporated
2. temperatureheated
3. additionwas added
4. temperaturethe mixture was heated
5. temperatureto reflux for 30 min
6. temperaturethe mixture was refluxed for another 30 min
7. customThe solvent was evaporated
8. customthe residue was partitioned between CH2Cl2 and aqueous Na2CO3 (10% w/v)
9. washThe organic layer was washed with H2O
10. dry with materialdried over MgSO4
11. customevaporated

ORD record

ord-53f2d3dc550e48d28a7eee8f86d6982d

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07414036B2