2-CHLORO-6-METHYL-4-NITROPYRIDINE 1-OXIDE synthesis

Yield:40314-84-9 75%

Reaction Conditions:

with sulfuric acid

Steps:

S.22.2 (2)

(2) Synthesis of 6-chloro-4-nitropicoline-N-oxide 98% Sulfuric acid (131 g, 0.207*6.3 mol) was added to 6-chloropicoline-N-oxide (29.7 g, 0.207 mol). To the resultant mixture was added 98% fuming sulfuric acid (72.34 g, 0.207*5 mol) and stirred at 100° C. for 1.5 hours. The reaction solution was then poured into iced water. A solid precipitate was filtered out, washed with water and dried to obtain 15.98 g of the target product. Furthermore, the filtrate was changed into weak alkalinity with sodium carbonate. A solid precipitate was filtered out, washed with water and dried to obtain 13.28 g of the target product. Percent yield: 75.0%, light yellow solid, m.p.: 118-121° C. IR KBr cm^-1: 1540, 1360, 1310, 1250, 920, 745. ¹H-NMR (60 MHz, CDCl₃, δ): 2.56 (3H, s, CH₃), 8.0 (1H, d, J=3 Hz, pyridine ring H), 8.2 (1H, d, J=3 Hz, pyridine ring H).

References:

US6610853,2003,B1