2-Chloro-4,6-dimethylpyridine

Light yellow liquid

A mixture of 2-amino-4Reference Example 48; 2-chloro-4, 6-dimethylpyridine; 2-Amino-4, 6-dimethyl-pyridine (4 g, 32.7 mmol) was dissolved in conc. hydrochloric acid (50 mL) and cooled to 0° C. A solution of sodium nitrite (3.39 g, 49.1 mmol) in water (20 mL) was added dropwise, followed by a solution of sodium chloride (3.8 g, 65 mmol) in water (20 mL). The mixture was stirred for 30 min. then basified with 20percent sodium hydroxide solution and extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo to give a residue which was purified by column chromatography on silica gel (60-120 mesh) using 5percent ethyl acetate/petroleum ether as eluent to afford 2-chloro-4, 6-dimethyl-pyridine (1 g, 22percent) as a solid.a) Preparation of 2-chloro-4, 6-dimethyl-pyridine. 2-Amino-4, 6-dimethyl-pyridine (4 g, 32.7 mmol) was dissolved in cone, hydrochloric acid (50 mL) and cooled to 0 EXAMPLE III 6-Chloro-2, 4-lutidine STR12 For the preparation of the title compound 'US 36 32[807], 600 g (4.91 mol) of 6-amino-2, 4-1utidine are dissolved in 2 l of methanol and the solution is saturated with hydrogen chloride gas at about 0 C. 1.307 l (9.82 mol) of isopentyl nitrite are added dropwise (about 2.5 h) at an intemal temperature of below 10 C. and the mixture is in this way for 15 h while warming to room temperature (about 25 C.). The solution is largely freed from the solvent in vacuo, mixed with 3 l of dichloromethane and 1.5 l of water and adjusted to pH=9.5 while cooling (<20 C.) with concentrated aqueous ammonia solution. The separated organic phase is dried with sodium sulphate, first concentrated in vacuo on a rotary evaporator and then distilled through a Vigreux column: Fraction 1) B.p.=47-49 C. (12 mm Hg), 603 g Fraction 2) B.p.=82-85 C. (12 mm Hg), 612 g (about 88% crude) Rf =0.39 (petroleum ether: ethyl acetate=10:1) 1 H-NMR (CDCl3 200 MHz, TMS): delta=2.28 (S, 3H), 2.47 (S, 3H), 6.88 (S, 1H), 6.96 (S, 1H) ppm.The following may be mentioned as examples of pyridine derivatives of the formula (IV): ... 2-chloro-4-methoxy-6-methyl-pyridine 2-chloro-4-methylmercapto-6-methyl-pyridine 2-chloro-3-cyano-6-methyl-pyridine 2-chloro-3, 6-dimethyl-pyridine 2-chloro-4, 6-dimethyl-pyridine 2-fluoro-4, 6-dimethyl-pyridine 2-chloro-6-methyl-4-propyl-pyridine 2-chloro-6-methyl-4-isopropyl-pyridine ...The following compounds may particularly be mentioned as examples of these substances: 2-chloro-4-methyl-pyridine 2-chloro-6-methyl-pyridine 2-chloro-4, 6-dimethyl-pyridine 2-chloro-4-methyl-pyrimidine 2-chloro-4-ethyl-pyrimidine 2-chloro-5-methyl-pyrimidine 2-chloro-5-ethyl-pyrimidine 2-chloro-5-propyl-pyrimidine 2-chloro-5-isopropyl-pyrimidine ...A solution of l-Boc-4-hydroxypiperidine (CAS: 109384-19-2; 1.00 g, 4.97 mmol) in anhydrous DMF (4.16 mL) was added dropwise to a stirred solution of NaH (60% dispersion in mineral oil, 238 mg, 5.96 mmol) in anhydrous DMF (4.16 mL) at 0 C. The mixture was stirred at 0 C for 30 min and a solution of

Molecular Weight:141.60
XLogP3:2.6
Hydrogen Bond Acceptor Count:1
Exact Mass:141.0345270
Monoisotopic Mass:141.0345270
Topological Polar Surface Area:12.9
Heavy Atom Count:9
Complexity:94.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes