4-chloro-2,6-dimethyl-1-oxidopyridin-1-ium

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the procedure of Example 1, Part B, but substituting 4-nitro-2,6-lutidine-1-oxide [as prepared by Ochiai, J. Org. Chem. 18, p. 534 (1953)] for 6-amino-4-nitro-2-picoline-1-oxide, there was prepared 4-chloro-2,6-lutidine-1-oxide hydrochloride.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the procedure of Example 1, Part B, but substituting 4-nitro-2,6-lutidine-1-oxide [as prepared by Ochiai, J. Org. Chem. 18, p. 534 (1953)] for 6-amino-4-nitro-2-picoline-1-oxide, there was prepared 4-chloro-2,6-lutidine-1-oxide hydrochloride.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4.0 g (25.4 mmol) of 4-chloro-2,6-dimethylpyridine-1-oxide was dissolved in 12 ml of acetic anhydride. The resultant solution was gradually heated to raise the temperature to the reflux temperature, and the solution was then stirred overnight at the same temperature. The reacted solution was then condensed under reduced pressure to obtain a crude product of acetic 4-chloro-6-methyl-2-pyridinylmethyl ester. to raise the temperature to the reflux temperature condensed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 12 g of (60% strength) NaH are added in portions to 50 ml of dry N-methylpyrrolidone (NMP). The mixture is stirred for 10 min. 19 g (0.22 mol) of 3-hydroxypropyl mercaptan are metered in the course of 30 min and the mixture is stirred for a further 30 min until evolution of gas has ended. A solution of 28.8 g (0.2 mol) of 4-chloro-2,6-dimethylpyridine-N-oxide in 150 ml of NMP is then added dropwise in the course of 30 min, and the reaction mixture is stirred for 1 h at RT, then for 1 h at 70° C. and after this for a further 1 h at 100° C. are metered in the course of 30 min the mixture is stirred for a further 30 min until evolution of gas the reaction mixture is stirred for 1 h at RT for 1 h at 70° C. for a further 1 h at 100° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the procedure of Example 1, Part B, but substituting 4-nitro-2,6-lutidine-1-oxide [as prepared by Ochiai, J. Org. Chem. 18, p. 534 (1953)] for 6-amino4-nitro-2-picoline-1-oxide, there was prepared 4-chloro-2,6-lutidine-1-oxide hydrochloride.