2-aminobenzene-1,3-diol

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: 100 mg of 2-aminobenzene-1,3-diol was dissolved in 2 ml of dichloromethane, and 234 μl of triethyl amine and 320 mg of p-toluene sulfonyl chloride were added and stirred at room temperature for 1.5 hours. To the reaction mixture, 20 ml of water was added, and extracted with 20 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to yield 278.1 mg of the title compound. extracted with 20 ml of ethyl acetate After the organic layer was dried over anhydrous magnesium sulfate the solvent was distilled off under reduced pressure purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

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

Procedure: 465 mg of 2-nitroresorcinol was dissolved in 9.3 ml of ethanol, and 230 mg of 10% palladium/carbon was added, and stirred under hydrogen atmosphere at room temperature for 1 hour. After the insoluble matter was filtered off, solvent was distilled off under reduced pressure to yield 338.5 mg of the title compound. After the insoluble matter was filtered off solvent was distilled off under reduced pressure

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

Procedure: 2-Nitroresorcinol (1.00 g, 6.45 mmol) was dissolved in ethanol (10 mL). The solution was then stirred for 6 hours at room temperature in the presence of 10% Pd/C (340 mg, 0.32 mmol) under hydrogen gas atmosphere. Insolubles were removed by filtration, and the solvent was distilled off under reduced pressure, to give 779 mg (yield 97%) of the desired compound in the form of a brown crystalline product. Insolubles were removed by filtration the solvent was distilled off under reduced pressure

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

Procedure: 2-Nitroresorcinol (1.00 g, 6.45 mmol) was dissolved in ethanol (10 mL). The solution was then stirred for 6 hours at room temperature in the presence of 10% Pd/C (340 mg, 0.32 mmol) under hydrogen gas atmosphere. Insolubles were removed by filtration, and the solvent was distilled off under reduced pressure, to give 779 mg (yield 97%) of the desired compound in the form of a brown crystalline product. Insolubles were removed by filtration the solvent was distilled off under reduced pressure

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

Procedure: 2-Nitroresorcinol (4.995 g, 0.032 mol) was suspended in ethanol (90 ml). Platinum(IV) oxide (0.356 g) was added and the mixture was shaken under an atmosphere of hydrogen (pH2 100 psi). After 2.75 hours (pH2 90 psi) the reaction mixture was filtered through celite. The residue was washed with methanol (50 ml) and the combined filtrate and washings were evaporated in vacuo at 30° C. During the course of the evaporation the solution, which was originally pale yellow, darkened considerably. A brown solid was obtained which was suspended in dichloromethane (100 ml) and re-evaporated to dryness. Yield 3.83 g (0.031 mol, 95%). After 2.75 hours (pH2 90 psi) the reaction mixture was filtered through celite The residue was washed with methanol (50 ml) the combined filtrate and washings were evaporated in vacuo at 30° C During the course of the evaporation the solution, which A brown solid was obtained which re-evaporated to dryness

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

Procedure: A suspension of 3-cyclopentyloxy-4-methoxyphenylacetic acid (2.49 g) and 1,1′-carbonyl diimidazole (2.31 g) in dichloromethane (10 ml) was stirred at room temperature, under argon, for 2 hours. The resulting solution was added to a stirred suspension of 2-aminoresorcinol (1.62 g) in dichloromethane (15 ml) and the mixture stirred at room temperature, under argon, overnight. The reaction mixture was diluted with water (100 ml) and extracted with dichloromethane (3×50 ml). The combined organic extracts were washed with water (100 ml), 1 N HCl (100 ml) and brine (100 ml), dried over CaSO4 and evaporated in-vacuo to yield the title compound (2.122 g, 60%) as a beige solid. the mixture stirred at room temperature, under argon, overnight extracted with dichloromethane (3×50 ml) The combined organic extracts were washed with water (100 ml), 1 N HCl (100 ml) and brine (100 ml) dried over CaSO4 evaporated in-vacuo

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

Procedure: A suspension of 2-nitroresorcinol (4.995 g) and platinum (IV) oxide (356 mg) in ethanol (90 ml) was hydrogenated, at room temperature, at 100 p.s.i. for 4 hours. The reaction mixture was filtered through celite, the filter cake washed with methanol (50 ml), and the combined filtrate evaporated in-vacuo to yield a brown solid. The solid was suspended in dichloromethane (100 ml) and evaporated to dryness to yield the title compound (3.83 g, 95%) as a brown solid. was hydrogenated, at room temperature, at 100 p.s.i The reaction mixture was filtered through celite the filter cake washed with methanol (50 ml) the combined filtrate evaporated in-vacuo to yield a brown solid evaporated to dryness

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

Procedure: A suspension of 2-nitroresorcinol (4.995 g) and platinum (IV) oxide (356 mg) in ethanol (90 ml) was hydrogenated, at room temperature, at 100 p.s.i. for 4 hours. The reaction mixture was filtered through celite, the filter cake washed with methanol (50 ml), and the combined filtrate evaporated in-vacuo to yield a brown solid. The solid was suspended in dichloromethane (100 ml) and evaporated to dryness to yield the title compound (3.83 g, 95%) as a brown solid. was hydrogenated, at room temperature, at 100 p.s.i The reaction mixture was filtered through celite the filter cake washed with methanol (50 ml) the combined filtrate evaporated in-vacuo to yield a brown solid evaporated to dryness

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

Procedure: 100 mg of 2-aminobenzene-1,3-diol was dissolved in 2 ml of dichloromethane, and 234 μl of triethyl amine and 320 mg of p-toluene sulfonyl chloride were added and stirred at room temperature for 1.5 hours. To the reaction mixture, 20 ml of water was added, and extracted with 20 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to yield 278.1 mg of the title compound. extracted with 20 ml of ethyl acetate After the organic layer was dried over anhydrous magnesium sulfate the solvent was distilled off under reduced pressure purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

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

Procedure: 100 mg of 2-aminobenzene-1,3-diol was dissolved in 2 ml of dichloromethane, and 234 μl of triethyl amine and 320 mg of p-toluene sulfonyl chloride were added and stirred at room temperature for 1.5 hours. To the reaction mixture, 20 ml of water was added, and extracted with 20 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to yield 278.1 mg of the title compound. extracted with 20 ml of ethyl acetate After the organic layer was dried over anhydrous magnesium sulfate the solvent was distilled off under reduced pressure purified by silica gel column chromatography (hexane:ethyl acetate=4:1)