4-methoxy-3-propan-2-ylaniline

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-isopropyl-4-methoxyaniline (4.22 g, 23.6 mmol), 5.87 g (63.7 mmole) of glycerol and 3.25 g (14 mmol) of As2O5 was heated to 100° C. with stirring At 100° C., 4.0 mL of concentrated H2SO4 was added dropwise. The mixture was heated at 150-160° C. for six hours, then cooled to 80° C., and 20 mL water was added, followed by aqueous saturated NaHCO3 until the mixture reached pH7-8. The mixture was diluted with 100 mL of water and 300 mL of ethyl acetate and the solution mixture was decanted from insolubles. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography with silica eluting with 20% ethyl acetate in hexanes to give 2.58 g of 7-isopropyl-6-methoxyquinoline, together with 0.65 g of 6-hydroxy-7-isopropylquinoline as a minority product. The mixture was heated at 150-160° C. for six hours cooled to 80° C. the solution mixture was decanted from insolubles The organic layer was separated washed with brine dried (MgSO4) filtered concentrated under reduced pressure The resulting residue was purified by column chromatography with silica eluting with 20% ethyl acetate in hexanes

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

Procedure: 2-Isopropyl-1-methoxy-4-nitro-benzene (4.53 g, 23.6 mmol) was dissolved in 100 mL of methanol in presence of 0.4 g of 10% Pd/C in a Parr bottle, and then subjected to 40 psi of H2 overnight at room temperature. The mixture was purged with nitrogen for 10 minutes and filtered over Celite. The filtrate was concentrated to give 4.22 g 3-isopropyl-4-methoxyaniline. subjected to 40 psi of H2 overnight at room temperature The mixture was purged with nitrogen for 10 minutes filtered over Celite The filtrate was concentrated

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

Procedure: 2-Isopropyl-1-methoxy-4-nitro-benzene (4.53 g, 23.6 mmol) was dissolved in 100 mL of methanol in presence of 0.4 g of 10% Pd/C in a Parr bottle, and then subjected to 40 psi of H2 overnight at room temperature. The mixture was purged with nitrogen for 10 minutes and filtered over Celite. The filtrate was concentrated to give 4.22 g 3-isopropyl-4-methoxyaniline. subjected to 40 psi of H2 overnight at room temperature The mixture was purged with nitrogen for 10 minutes filtered over Celite The filtrate was concentrated

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-isopropyl-4-methoxyaniline (4.22 g, 23.6 mmol), 5.87 g (63.7 mmole) of glycerol and 3.25 g (14 mmol) of As2O5 was heated to 100° C. with stirring At 100° C., 4.0 mL of concentrated H2SO4 was added dropwise. The mixture was heated at 150-160° C. for six hours, then cooled to 80° C., and 20 mL water was added, followed by aqueous saturated NaHCO3 until the mixture reached pH7-8. The mixture was diluted with 100 mL of water and 300 mL of ethyl acetate and the solution mixture was decanted from insolubles. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography with silica eluting with 20% ethyl acetate in hexanes to give 2.58 g of 7-isopropyl-6-methoxyquinoline, together with 0.65 g of 6-hydroxy-7-isopropylquinoline as a minority product. The mixture was heated at 150-160° C. for six hours cooled to 80° C. the solution mixture was decanted from insolubles The organic layer was separated washed with brine dried (MgSO4) filtered concentrated under reduced pressure The resulting residue was purified by column chromatography with silica eluting with 20% ethyl acetate in hexanes

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

Procedure: 2-Isopropyl-1-methoxy-4-nitro-benzene (4.53 g, 23.6 mmol) was dissolved in 100 mL of methanol in presence of 0.4 g of 10% Pd/C in a Parr bottle, and then subjected to 40 psi of H2 overnight at room temperature. The mixture was purged with nitrogen for 10 minutes and filtered over Celite. The filtrate was concentrated to give 4.22 g 3-isopropyl-4-methoxyaniline. subjected to 40 psi of H2 overnight at room temperature The mixture was purged with nitrogen for 10 minutes filtered over Celite The filtrate was concentrated