4-chloro-2-propan-2-yloxyaniline

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

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of Compound 35A (1 g) in methanol (30 mL) was added Raney-Ni (0.05 g) and the resulting mixture was cooled at 0-5° C.; 98% hydrazine hydrate (1.5 mL) was dropped in at the same temperature and the suspension stirred at room temperature for 2 h. The catalyst was filtered off and the solvents evaporated in vacuo. The crude was dissolved in dichloromethane (100 mL) and washed with water (60 mL); the organic layer was dried over sodium sulphate and evaporated to dryness affording 0.78 g (90%) of the title product as a yellow oil. The catalyst was filtered off the solvents evaporated in vacuo The crude was dissolved in dichloromethane (100 mL) washed with water (60 mL) the organic layer was dried over sodium sulphate evaporated to dryness

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2.55 g of 4-chloro-1-nitro-2-(propan-2-yloxy)benzene in 40 ml of acetic acid is heated at 50° C., and then 7 ml of water and 2.64 g of iron powder are added. The mixture is stirred for 1 h at 50° C., and then cooled to ambient temperature and filtered on Celite. The Celite is rinsed three times with 20 ml of methanol, and the filtrate is concentrated under reduced pressure. The residue is taken up in 50 ml of 1N sodium hydroxide and 50 ml of dichloromethane. The aqueous phase is extracted twice with 50 ml of dichloromethane. The combined organic phases are dried over anhydrous magnesium sulfate, filtered and then concentrated to dryness under reduced pressure, so as to obtain 2.25 g of 4-chloro-2-(propan-2-yloxy)aniline in the form of a green oil. cooled to ambient temperature filtered on Celite The Celite is rinsed three times with 20 ml of methanol the filtrate is concentrated under reduced pressure The aqueous phase is extracted twice with 50 ml of dichloromethane The combined organic phases are dried over anhydrous magnesium sulfate filtered concentrated to dryness under reduced pressure

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2.55 g of 4-chloro-1-nitro-2-(propan-2-yloxy)benzene in 40 ml of acetic acid is heated at 50° C., and then 7 ml of water and 2.64 g of iron powder are added. The mixture is stirred for 1 h at 50° C., and then cooled to ambient temperature and filtered on Celite. The Celite is rinsed three times with 20 ml of methanol, and the filtrate is concentrated under reduced pressure. The residue is taken up in 50 ml of 1N sodium hydroxide and 50 ml of dichloromethane. The aqueous phase is extracted twice with 50 ml of dichloromethane. The combined organic phases are dried over anhydrous magnesium sulfate, filtered and then concentrated to dryness under reduced pressure, so as to obtain 2.25 g of 4-chloro-2-(propan-2-yloxy)aniline in the form of a green oil. cooled to ambient temperature filtered on Celite The Celite is rinsed three times with 20 ml of methanol the filtrate is concentrated under reduced pressure The aqueous phase is extracted twice with 50 ml of dichloromethane The combined organic phases are dried over anhydrous magnesium sulfate filtered concentrated to dryness under reduced pressure

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of Compound 35A (1 g) in methanol (30 mL) was added Raney-Ni (0.05 g) and the resulting mixture was cooled at 0-5° C.; 98% hydrazine hydrate (1.5 mL) was dropped in at the same temperature and the suspension stirred at room temperature for 2 h. The catalyst was filtered off and the solvents evaporated in vacuo. The crude was dissolved in dichloromethane (100 mL) and washed with water (60 mL); the organic layer was dried over sodium sulphate and evaporated to dryness affording 0.78 g (90%) of the title product as a yellow oil. The catalyst was filtered off the solvents evaporated in vacuo The crude was dissolved in dichloromethane (100 mL) washed with water (60 mL) the organic layer was dried over sodium sulphate evaporated to dryness

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of Compound 35A (1 g) in methanol (30 mL) was added Raney-Ni (0.05 g) and the resulting mixture was cooled at 0-5° C.; 98% hydrazine hydrate (1.5 mL) was dropped in at the same temperature and the suspension stirred at room temperature for 2 h. The catalyst was filtered off and the solvents evaporated in vacuo. The crude was dissolved in dichloromethane (100 mL) and washed with water (60 mL); the organic layer was dried over sodium sulphate and evaporated to dryness affording 0.78 g (90%) of the title product as a yellow oil. The catalyst was filtered off the solvents evaporated in vacuo The crude was dissolved in dichloromethane (100 mL) washed with water (60 mL) the organic layer was dried over sodium sulphate evaporated to dryness

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2.55 g of 4-chloro-1-nitro-2-(propan-2-yloxy)benzene in 40 ml of acetic acid is heated at 50° C., and then 7 ml of water and 2.64 g of iron powder are added. The mixture is stirred for 1 h at 50° C., and then cooled to ambient temperature and filtered on Celite. The Celite is rinsed three times with 20 ml of methanol, and the filtrate is concentrated under reduced pressure. The residue is taken up in 50 ml of 1N sodium hydroxide and 50 ml of dichloromethane. The aqueous phase is extracted twice with 50 ml of dichloromethane. The combined organic phases are dried over anhydrous magnesium sulfate, filtered and then concentrated to dryness under reduced pressure, so as to obtain 2.25 g of 4-chloro-2-(propan-2-yloxy)aniline in the form of a green oil. cooled to ambient temperature filtered on Celite The Celite is rinsed three times with 20 ml of methanol the filtrate is concentrated under reduced pressure The aqueous phase is extracted twice with 50 ml of dichloromethane The combined organic phases are dried over anhydrous magnesium sulfate filtered concentrated to dryness under reduced pressure