1-(4-aminophenyl)-2-methylpropan-1-one

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: A mixture of 1-(4-aminophenyl)-2-methyl-1-propanone (0.0637 mol) and methyl 2-chloro-3-pyridinecarboxylate (0.0637 mol) in 2-methoxyethanol (200 ml) was stirred and refluxed for 90 hours. The mixture was taken up in water and EtOAc and extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 22.6 g of methyl 2[[4-(2-methyl-1-oxopropyl)phenyl]amino]-3-pyridinecarboxylate (interm. 20). refluxed for 90 hours EtOAc and extracted with EtOAc The organic layer was separated dried filtered the solvent was evaporated

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: p-Nitroisobutyrophenone from step 4 (1.0 g, 0.0058 mol), was dissolved in DMF (5 ml). SnCl2.2H2O (4.67 g, 0.0207 mol) is added and the reaction is stirred at room temperature. After 4 hours the reaction was poured into 100 ml of ethyl acetate. Excess Et3N (4 ml) was added and a white, solid precipitate formed. The suspension was filtered through celite. Evaporation of the filtrate left a yellow solid which was purified by column chromatography. The resulting crystalline solid (0.700 g, 4.2 mmol, 82%) had a 1H-NMR (DMSO): 7.71 (d, 2H), 6.58 (d, 2H), 6.03 (s, 2H), 3.45 (m, 1H), 1.06 (s, 6H) a white, solid precipitate formed The suspension was filtered through celite Evaporation of the filtrate left a yellow solid which was purified by column chromatography

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

Procedure: p-Nitroisobutyrophenone from step 4 (1.0 g, 0.0058 mol), was dissolved in DMF (5 ml). SnCl2.2H2O (4.67 g, 0.0207 mol) is added and the reaction is stirred at room temperature. After 4 hours the reaction was poured into 100 ml of ethyl acetate. Excess Et3N (4 ml) was added and a white, solid precipitate formed. The suspension was filtered through celite. Evaporation of the filtrate left a yellow solid which was purified by column chromatography. The resulting crystalline solid (0.700 g, 4.2 mmol, 82%) had a 1H-NMR (DMSO): 7.71 (d, 2H), 6.58 (d, 2H), 6.03 (s, 2H), 3.45 (m, 1H), 1.06 (s, 6H) a white, solid precipitate formed The suspension was filtered through celite Evaporation of the filtrate left a yellow solid which was purified by column chromatography

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

Procedure: A mixture of 1-(4-aminophenyl)-2-methyl-1-propanone (0.0637 mol) and methyl 2-chloro-3-pyridinecarboxylate (0.0637 mol) in 2-methoxyethanol (200 ml) was stirred and refluxed for 90 hours. The mixture was taken up in water and EtOAc and extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 22.6 g of methyl 2-[[4-(2-methyl-1-oxopropyl)phenyl]amino]-3-pyridinecarboxylate (interm. 20). refluxed for 90 hours EtOAc and extracted with EtOAc The organic layer was separated dried filtered the solvent was evaporated

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

Procedure: A mixture of 1-(4-aminophenyl)-2-methyl-1-propanone (0.0637 mol) and methyl 2-chloro-3-pyridinecarboxylate (0.0637 mol) in 2-methoxyethanol (200 ml) was stirred and refluxed for 90 hours. The mixture was taken up in water and EtOAc and extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 22.6 g of methyl 2-[[4-(2-methyl-1-oxopropyl)phenyl]amino]-3-pyridinecarboxylate (interm. 20). refluxed for 90 hours EtOAc and extracted with EtOAc The organic layer was separated dried filtered the solvent was evaporated

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

Procedure: A mixture of 1-(4-aminophenyl)-2-methyl-1-propanone (0.0637 mol) and methyl 2-chloro-3-pyridinecarboxylate (0.0637 mol) in 2-methoxyethanol (200 ml) was stirred and refluxed for 90 hours. The mixture was taken up in water and EtOAc and extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 22.6 g of methyl 2-[[4-(2-methyl-1-oxopropyl)phenyl]amino]-3-pyridinecarboxylate (interm. 20). refluxed for 90 hours EtOAc and extracted with EtOAc The organic layer was separated dried filtered the solvent was evaporated

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

Procedure: A mixture of 1-(4-aminophenyl)-2-methyl-1-propanone (0.0637 mol) and methyl 2chloro-3-pyridinecarboxylate (0.0637 mol) in 2-methoxyethanol (200 ml) was stirred and refluxed for 90 hours. The mixture was taken up in water and EtOAc and extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 22.6 g of methyl 2-[[4-(2-methyl-1-oxopropyl)phenyl]amino]-3-pyridinecarboxylate (interm. 20). refluxed for 90 hours EtOAc and extracted with EtOAc The organic layer was separated dried filtered the solvent was evaporated

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

Procedure: A mixture of 1-(4-aminophenyl)-2-methyl-1-propanone (0.0637 mol) and methyl 2chloro-3-pyridinecarboxylate (0.0637 mol) in 2-methoxyethanol (200 ml) was stirred and refluxed for 90 hours. The mixture was taken up in water and EtOAc and extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 22.6 g of methyl 2-[[4-(2-methyl-1-oxopropyl)phenyl]amino]-3-pyridinecarboxylate (interm. 20). refluxed for 90 hours EtOAc and extracted with EtOAc The organic layer was separated dried filtered the solvent was evaporated