2-amino-4-chloro-5-methylphenol

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 4-chloro-5-methyl-2-nitrophenol (5.0 g) in methanol (100 mL) at 0° C. was added zinc powder (8.71 g), which was activated by hydrochloric acid in advance, and a solution of ammonium chloride (7.1 g) in water (20 mL). The suspension was stirred for 4 h at room temperature. Then the insoluble material was filtered off through celite, and the celite cake was washed with ethyl acetate (100 mL). The filtrate and washings were combined and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using hexane/ethyl acetate (3:2) to yield the title compound (1.4 g). Then the insoluble material was filtered off through celite the celite cake was washed with ethyl acetate (100 mL) concentrated under reduced pressure The residue was purified by column chromatography over silica gel

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

Procedure: To a solution of 4-chloro-5-methyl-2-nitrophenol (5.0 g) in methanol (100 mL) at 0° C. was added zinc powder (8.71 g), which was activated by hydrochloric acid in advance, and a solution of ammonium chloride (7.1 g) in water (20 mL). The suspension was stirred for 4 h at room temperature. Then the insoluble material was filtered off through celite, and the celite cake was washed with ethyl acetate (100 mL). The filtrate and washings were combined and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using hexane/ethyl acetate (3:2) to yield the title compound (1.4 g). Then the insoluble material was filtered off through celite the celite cake was washed with ethyl acetate (100 mL) concentrated under reduced pressure The residue was purified by column chromatography over silica gel

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

Procedure: To a solution of 4-chloro-5-methyl-2-nitrophenol (5.0 g) in methanol (100 mL) at 0° C. was added zinc powder (8.71 g), which was activated by hydrochloric acid in advance, and a solution of ammonium chloride (7.1 g) in water (20 mL). The suspension was stirred for 4 h at room temperature. Then the insoluble material was filtered off through celite, and the celite cake was washed with ethyl acetate (100 mL). The filtrate and washings were combined and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using hexane/ethyl acetate (3:2) to yield the title compound (1.4 g). Then the insoluble material was filtered off through celite the celite cake was washed with ethyl acetate (100 mL) concentrated under reduced pressure The residue was purified by column chromatography over silica gel

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

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

Procedure: To 30 ml of methanol, there were added 1.0 g (6.4 mmol) of 2-amino-4-chloro-5-methylphenol and 0.71 g (7.0 mmol) of acetic anhydride and stirred at room temperature for 30 minutes. To this solution, there was added 60 ml of water. The crystals thus precipitated were filtered and recrystallized from methanol. Thus 0.89 g (4.5 mmol) of N-(5-chloro-2-hydroxy-4-methylphenyl)acetamide was obtained as pale brown crystals. The yield was 70%. The crystals thus precipitated were filtered recrystallized from methanol

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

Procedure: To 15 ml of a solvent mixture of water-ethanol (1:1 (v:v)), there was added 0.5 ml of glacial acetic acid and heated under reflux. To the obtained solution, there were added 0.86 g of iron powder and 0.80 g (4.3 mmol) of 4-chloro-5-methyl-2-nitrophenol and the mixture was heated under reflux for additional 20 minutes. After cooling and adding 30 ml of acetone, the iron powder was filtered and washed with 50 ml of acetone. The filtrate was combined with the washing liquor and the solvent was distilled off therefrom under reduced pressure to thereby give a brown solid. The obtained product was subjected to silica gel column chromatography (Si60 manufactured by Merck; 230-400 mesh; 200 g; eluent: hexane-ethyl acetate (2:1 (v:v)). The solvent was distilled off from the 1,100-2,000 ml fraction and thus 0.29 g (1.8 mmol) of 2-amino-4-chloro-5-methylphenol was obtained as yellow crystals. The yield was 43%. heated under reflux the mixture was heated under reflux for additional 20 minutes After cooling the iron powder was filtered washed with 50 ml of acetone the solvent was distilled off under reduced pressure to thereby give a brown solid The solvent was distilled off from the 1,100-2,000 ml fraction

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

Procedure: To a solution of 4-chloro-5-methyl-2-nitrophenol (5.0 g) in methanol (100 mL) at 0° C. was added zinc powder (8.71 g), which was activated by hydrochloric acid in advance, and a solution of ammonium chloride (7.1 g) in water (20 mL). The suspension was stirred for 4 h at room temperature. Then the insoluble material was filtered off through celite, and the celite cake was washed with ethyl acetate (100 mL). The filtrate and washings were combined and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using hexane/ethyl acetate (3:2) to yield the title compound (1.4 g). Then the insoluble material was filtered off through celite the celite cake was washed with ethyl acetate (100 mL) concentrated under reduced pressure The residue was purified by column chromatography over silica gel