2-CHLOROMETHYL-3-METHYL-PYRIDINEHYDROCHLORIDE

To a stirred solution of 2, 3-lutidine (5.00 g, 46.7 mmol) in chloroform (100 mL) at 0°C was added m- chloroperbenzoic acid (12.0 g of a 77percent max reagent) portionwise over 5 min. The reaction mixture was stirred for an additional 30 min at 0°C and then allowed to warm to room temperature. After 16 h, the reaction mixture was concentrated to dryness, water (20 mL) was added and the pH of the mixture was adjusted to 8 (saturated NaHCO3). The mixture was concentrated and the residue was extracted with dichloromethane/methanol (4: 1). The extracts were concentrated to a white solid. Subsequent column purification (Si02 ; dichloromethane/methanol, 9: 1) gave 2, 3-lutidine-N-oxide as a white solid (4.80 g, 83percent). A stirred solution of 2, 3-lutidine-N-oxide (4.80 g, 39.0 mmol) in acetic anhydride (50 mL) was heated under reflux overnight, cooled and then concentrated to dryness providing (2-acetoxymethyl) -3-methylpyridine as a brown oil (6.34 g). A mixture of the crude (2-acetoxymethyl)-3- methylpyridine and K2CO3 (10. 0 g, 72.4 mmol), methanol (60 mL) and water (30 mL) was stirred at room temperature overnight. The solid was filtered off and the filtrate was concentrated to dryness. The residue, after column chromatography (Si02 ; dichloromethane/methanol, 9: 1), gave (2-hydroxymethyl) -3-methylpyridine as a light brown oil (2.86 g, 59percent over 2 steps). (2-Hydroxymethyl) -3-methylpyridine: 1H NMR (CDC13) : 5 8.41 (d, J = 4.9, 1 H), 7.48 (d, J = 7.5, 1 H), 7.16 (dd, J = 4.9 and 7.5, 1 H), 4.69 (s, 2 H), 4.00 (br, 1 H), 2.22 (s, 3 H).

Molecular Weight:178.06
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:177.0112047
Monoisotopic Mass:177.0112047
Topological Polar Surface Area:12.9
Heavy Atom Count:10
Complexity:85
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes