1,2-dimethylhydrazine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Diethyl methylmalonate and N,N'-dimethylhydrazine are heated under reflux for 170 hours in methanol in the presence of sodium methylate under an atmosphere of nitrogen. 3-Hydroxy-1,2,4-trimethyl-5-pyrazolone is obtained in the form of colorless crystals which, after recrystallization from ethyl acetate, melt at 87°-89° C.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of 36 g (0.60 mole) of dimethylhydrazine and 150 ml of benzene was added portionwise 60 g (0.25 mole) of 5-(p-chlorophenyl)-2-furoyl chloride with the temperature being controlled below 50° by means of an ice bath. The reaction mixture was refluxed for 2 hours with dissolution, cooled and the resulting precipitate filtered, washed with water and dried at 60° to yield 48 g (73%). An analytical sample was prepared by recrystallizing a sample from ethyl acetate/Darco and drying in the vacuum pistol at room temperature, m.p. 150°-152°. being controlled below 50° by means of an ice bath The reaction mixture was refluxed for 2 hours with dissolution cooled the resulting precipitate filtered washed with water dried at 60° to yield 48 g (73%) An analytical sample was prepared by recrystallizing a sample from ethyl acetate/Darco drying in the vacuum pistol at room temperature

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(2-methoxy-4-nitrophenyl)pyridine (5.4 g, 23.3 mmol), dimethyl hydrazine (14 mL, 233 mmol), charcoal (0.7 g), in methanol (200 mL) was added iron trichloride (0.075 g, 0.46 mmol), then heated at 65° C. overnight. The reaction mixture was quenched with H2O (50 mL), then extracted with EtOAc (3×50 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude purified by liquid chromatography on silica (EtOAc/Hexane 3/7) to give 3-methoxy-4-pyridin-2-ylaniline. The reaction mixture was quenched with H2O (50 mL) extracted with EtOAc (3×50 mL) the combined organic extracts washed with brine The organic phase was dried over Na2SO4 concentrated in vacuo The crude purified by liquid chromatography on silica (EtOAc/Hexane 3/7)

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(2-methoxy-4-nitrophenyl)pyridine (5.4 g, 23.3 mmol), dimethyl hydrazine (14 mL, 233 mmol), charcoal (0.7 g), in methanol (200 mL) was added iron trichloride (0.075 g, 0.46 mmol), then heated at 65° C. overnight. The reaction mixture was quenched with H2O (50 mL), then extracted with EtOAc (3×50 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude purified by liquid chromatography on silica (EtOAc/Hexane 3/7) to give 3-methoxy-4-pyridin-2-ylaniline. The reaction mixture was quenched with H2O (50 mL) extracted with EtOAc (3×50 mL) the combined organic extracts washed with brine The organic phase was dried over Na2SO4 concentrated in vacuo The crude purified by liquid chromatography on silica (EtOAc/Hexane 3/7)

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

Procedure: A solution of 3-cyano-1-[4-fluoro-benzoyl]-pyrrolo[1,2-a]quinoline (56 mg, 0.18 mmol) and dimethylhydrazine (118 mg, 1.96 mmol) in DMF (5 mL) was refluxed for 24 h. It was diluted with water (50 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were dried, concentrated and the residue was purified by column chromatography (EtOAc/Hexane 6:1) to give 15 mg (25%) of the title compound. 1H NMR (CDCl3): 8.11–8.05–7.95 (m, 3H), 7.82–7.78 (m, 2H), 7.63–7.42 (m, 4H), 7.31 (s, 1H), 6.75 (d, J=9.30 Hz, 2H), 3.14 (s, 6H). MS, 340 (M+1). extracted with EtOAc (3×20 mL) The combined organic layers were dried concentrated the residue was purified by column chromatography (EtOAc/Hexane 6:1)

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

Procedure: A solution of 3-cyano-1-[4-fluoro-benzoyl]-pyrrolo[1,2-a]quinoline (56 mg, 0.18 mmol) and dimethylhydrazine (118 mg, 1.96 mmol) in DMF (5 mL) was refluxed for 24 h. It was diluted with water (50 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were dried, concentrated and the residue was purified by column chromatography (EtOAc/Hexane 6:1) to give 15 mg (25%) of the title compound. 1H NMR (CDCl3): 8.11–8.05–7.95 (m, 3H), 7.82–7.78 (m, 2H), 7.63–7.42 (m, 4H), 7.31 (s, 1H), 6.75 (d, J=9.30 Hz, 2H), 3.14 (s, 6H). MS, 340 (M+1). extracted with EtOAc (3×20 mL) The combined organic layers were dried concentrated the residue was purified by column chromatography (EtOAc/Hexane 6:1)

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

Procedure: Diethyl methylmalonate and N,N'-dimethylhydrazine are heated under reflux for 170 hours in methanol in the presence of sodium methylate under an atmosphere of nitrogen. 3-Hydroxy-1,2,4-trimethyl-5-pyrazolone is obtained in the form of colorless crystals which, after recrystallization from ethyl acetate, melt at 87°-89° C.

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

Procedure: Diethyl methylmalonate and N,N'-dimethylhydrazine are heated under reflux for 170 hours in methanol in the presence of sodium methylate under an atmosphere of nitrogen. 3-Hydroxy-1,2,4-trimethyl-5-pyrazolone is obtained in the form of colorless crystals which, after recrystallization from ethyl acetate, melt at 87°-89° C.