2-methyl-1-oxidopyridin-1-ium

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

Procedure: A solution of 2-picoline N-oxide (4.4 g, 0.04 mol) in benzene (25 ml) was added to a suspension of sodium hydride (3.2 g of 60% oil dispersion) and methyl benzoate (9.94 ml, 0.08 mol) in dry benzene (100 ml). The reaction mixture was refluxed overnight. Methanol (15 ml) was added to the cooled reaction mixture, followed by water (150 ml). The aqueous layer was separated and extracted with chloroform (2×40 ml). The aqueous layer was acidified with 1N HCl and extracted with chloroform. The combined organic layers were dried (MgSO4) and concentrated to give the subtitle ketone as a solid (7 g), mp 146°-148° C. The reaction mixture was refluxed overnight The aqueous layer was separated extracted with chloroform (2×40 ml) extracted with chloroform The combined organic layers were dried (MgSO4) concentrated

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

Procedure: Following, the general method described in example 2a, 2-picoline-1-oxide was reacted with potassium tert.-butanolate and 3-fluoro-benzaldehyde. After extraction and chromatography the title compound was obtained as a yellow solid material. MS: m/e=215 (M+). After extraction and chromatography the title compound was obtained as a yellow solid material

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

Procedure: Following the general method described in example 2a, 2-picoline-1-oxide was reacted with potassium tert.-butanolate and 2-fluoro-benzaldehyde. After extraction and chromatography the title compound was obtained as a yellow solid material. MS: m/e=215 (M+). After extraction and chromatography the title compound was obtained as a yellow solid material

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

Procedure: Following the general method described in example 2a, 2-picoline-1-oxide was reacted with potassium tert.-butanolate and 2-fluoro-benzaldehyde. After extraction and chromatography the title compound was obtained as a yellow solid material. MS: m/e=215 (M+). After extraction and chromatography the title compound was obtained as a yellow solid material

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

Procedure: Following the general method described in example 2a, 2-picoline-1-oxide was reacted with potassium tert.-butanolate and 3-chloro-benzaldehyde. After extraction and chromatography the title compound was obtained as a yellow solid material. MS: m/e=231 (M+). After extraction and chromatography the title compound was obtained as a yellow solid material

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

Procedure: Following, the general method described in example 2a, 2-picoline-1-oxide was reacted with potassium tert.-butanolate and 4-fluoro-benzaldehyde. After extraction and chromatography the title compound was obtained as a yellow solid material. MS: m/e=215 (M+). After extraction and chromatography the title compound was obtained as a yellow solid material

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

Procedure: Following, the general method described in example 2a, 2-picoline-1-oxide was reacted with potassium tert.-butanolate and 4-fluoro-benzaldehyde. After extraction and chromatography the title compound was obtained as a yellow solid material. MS: m/e=215 (M+). After extraction and chromatography the title compound was obtained as a yellow solid material

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

Procedure: Following the general method described in example 2a, 2-picoline-1-oxide was reacted with potassium tert.-butanolate and 3,4-dichloro-benzaldehyde. After extraction and chromatography the title compound was obtained as a yellow solid material. MS: m/e=265 (M+). After extraction and chromatography the title compound was obtained as a yellow solid material

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

Procedure: Following the general method described in example 2a, 2-picoline-1-oxide was reacted with potassium tert.-butanolate and 4-chloro-benzaldehyde. After extraction and chromatography the title compound was obtained as a yellow solid material. MS: m/e=231 (M+). After extraction and chromatography the title compound was obtained as a yellow solid material

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

Procedure: Following the general method described in example 2a, 2-picoline-1-oxide was reacted with potassium tert.-butanolate and p-anisaldehyde. After extraction and chromatography the title compound was obtained as a yellow solid material. MS: m/e=227 (M+). After extraction and chromatography the title compound was obtained as a yellow solid material

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

Procedure: To a refluxing solution of 2-picoline-1-oxide (10.9 g, 100 mmol), potassium tert.-butanolate ( 11.2 g, 100 mmol) in butanol (100 ml) was added portion-wise p-tolualdehyde (12.0 g, 100 mmol). Reflux was maintained for 90 min. Then the mixture was cooled to rt, diluted with H2O (100 ml) and extracted with CH2Cl2. The combined organic phases were dried with MgSO4, concentrated and chromatographed (SiO2 with CH2Cl2/MeOH=95:5) to provide the title compound (11.6 g, 55%) as a yellow solid material. MS: m/e=211 (M+). Reflux was maintained for 90 min extracted with CH2Cl2 The combined organic phases were dried with MgSO4 concentrated chromatographed (SiO2 with CH2Cl2/MeOH=95:5)

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

Procedure: To a refluxing solution of 2-picoline-1-oxide (10.9 g, 100 mmol), potassium tert.-butanolate ( 11.2 g, 100 mmol) in butanol (100 ml) was added portion-wise p-tolualdehyde (12.0 g, 100 mmol). Reflux was maintained for 90 min. Then the mixture was cooled to rt, diluted with H2O (100 ml) and extracted with CH2Cl2. The combined organic phases were dried with MgSO4, concentrated and chromatographed (SiO2 with CH2Cl2/MeOH=95:5) to provide the title compound (11.6 g, 55%) as a yellow solid material. MS: m/e=211 (M+). Reflux was maintained for 90 min extracted with CH2Cl2 The combined organic phases were dried with MgSO4 concentrated chromatographed (SiO2 with CH2Cl2/MeOH=95:5)