(3-amino-2-methylphenyl)methanol

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

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

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

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: Acetic anhydride (1.68 mL, 17.8 mmol) was added to a suspension of 3-amino-2-methylbenzyl alcohol (0.82 g, 5.98 mmol) in chloroform (25 mL). Potassium acetate was added and the resulting mixture was stirred at room temperature for 3 h, under reflux for 2 h, and then at room temperature overnight. Amyl nitrite (1.82 mL, 13.7 mmol) and 18-crown-6 (79 mg, 0.3 mmol) were added and the pale yellow cloudy mixture was heated at reflux overnight, then allowed to cool to room temperature and stir for 5 h. The reaction mixture was poured into acetic anhydride (5 mL) and stirred at room temperature overnight. Dichloromethane (20 mL) was added and the solution was washed with sodium hydrogen carbonate solution, water, and brine (10 mL each), dried (Na2SO4), filtered, concentrated, and chromatographed (10-40% ethyl acetate/petroleum ether) to give 1-acetyl-1H-indazole-4-methanol, acetate ester (1.19 g, 86%) as a pale yellow solid. under reflux for 2 h at room temperature overnight the pale yellow cloudy mixture was heated at reflux overnight to cool to room temperature stir for 5 h stirred at room temperature overnight the solution was washed with sodium hydrogen carbonate solution, water, and brine (10 mL each) dried (Na2SO4) filtered concentrated chromatographed (10-40% ethyl acetate/petroleum ether)

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

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

Procedure: A solution of 3-butyryl-4-chloro-8-methoxyquinoline (1.32 g, 5 mmol) and 3-amino-2-methylbenzyl alcohol (0.82 g, 6 mmol) in dioxan (25 ml) was heated at reflux for 1.5 hours, then the solvent evaporated. Aqueous sodium bicarbonate was added, the product extracted into dichloromethane, dried and evaporated. Recrystallisation from methanol gave 3-butyryl-4-(3-hydroxymethyl-2-methylphenylamino)-8-methoxyquinoline (1.20 g, 66%), m.p. 186°-188°. at reflux for 1.5 hours the solvent evaporated Aqueous sodium bicarbonate was added the product extracted into dichloromethane dried evaporated Recrystallisation from methanol

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

Procedure: A solution of 3-butyryl-4-chloro-8-methoxyquinoline (1.32 g, 5 mmol) and 3-amino-2-methylbenzyl alcohol (0.82 g, 6 mmol) in dioxan (25 ml) was heated at reflux for 1.5 hours, then the solvent evaporated. Aqueous sodium bicarbonate was added, the product extracted into dichloromethane, dried and evaporated. Recrystallisation from methanol gave 3-butyryl-4-(3-hydroxymethyl-2-methylphenylamino)-8-methoxyquinoline (1.20 g, 66%), m.p. 186°-188°. at reflux for 1.5 hours the solvent evaporated Aqueous sodium bicarbonate was added the product extracted into dichloromethane dried evaporated Recrystallisation from methanol

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

Procedure: A solution of 2-methyl-3-nitrobenzyl alcohol (2.0 g, 12 mmol) in ethanol (100 ml) was hydrogenated over 10% palladium/charcoal (0.1 g) for 2 hours, at an initial pressure of 3.5 bar. The solution was filtered through celite and evaporated to give 3-amino-2-methylbenzyl alcohol (1.67 g, quantitative), m.p. 104°-106° The solution was filtered through celite evaporated

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

Procedure: Prepared according to the method of Example 1b) from 1-adamantaneacetyl chloride (2.0 g) and 3-amino-2-methylbenzyl alcohol (1.29 g). Silica gel chromatography, eluting with 5% ethylacetate in dichloromethane gave the title compound as a white solid (0.80 g). Prepared Silica gel chromatography, eluting with 5% ethylacetate in dichloromethane

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

Procedure: Prepared according to the method of Example 1b) from 1-adamantaneacetyl chloride (2.0 g) and 3-amino-2-methylbenzyl alcohol (1.29 g). Silica gel chromatography, eluting with 5% ethylacetate in dichloromethane gave the title compound as a white solid (0.80 g). Prepared Silica gel chromatography, eluting with 5% ethylacetate in dichloromethane