(3-amino-4-methylphenyl)methanol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 3-butyryl-4-chloro-8-methoxyquinoline (0.80 g, 3 mmol) and 3-amino-4-methylbenzyl alcohol (0.48 g, 3.5 mmol) in dioxan (I0 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-(5-hydroxymethyl-2-methylphenylamino)-8-methoxyquinoline (0.65 g, 59%) 180°-181°. at reflux for 1.5 hours the solvent evaporated Aqueous sodium bicarbonate was added the product extracted into dichloromethane dried evaporated Recrystallisation from methanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl 3-amino-4-methylbenzoate (16.52 g, 0.1 mol) was dissolved in diglyme (150 ml), lithium borohydride (2.18 g, 0.1 mol) added, and the solution stirred at room temperature overnight. A further portion of lithium borohydride (2.18 g, 0.1 mol) was added, and the mixture heated at reflux for 20 minutes. The reaction was quenched with water, the solvent evaporated, the residue dissolved in water, the solution adjusted to pH 5 with hydrochloric acid, and the product extracted into dichloromethane. Drying, evaporation and trituration with ether gave 3-amino-4-methylbenzyl alcohol (7.3 g, 54%), m.p. 105°-107°. the mixture heated at reflux for 20 minutes The reaction was quenched with water the solvent evaporated the residue dissolved in water the product extracted into dichloromethane Drying evaporation and trituration with ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Prepared according to the method of Example 1b) from 1-adamantaneacetyl chloride (2.0 g) and 3-amino4-methylbenzyl alcohol (1.29 g). Silica gel chromatography, eluting with 5% ethylacetate in dichloromethane gave the title compound as a white solid (1.10 g). Prepared Silica gel chromatography, eluting with 5% ethylacetate in dichloromethane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred, cooled (0° C.) mixture of 3-amino-4-methylbenzyl alcohol (10.0 g, 0.072 mol) and pyridine (5.8 g, 0.072 mol) in THF (100 ML) was added 3-nitrobenzoyl chloride (13.5 g, 0.072 mol). After 2 h, the mixture was concentrated, suspended in water and filtered to give a brown solid. Trituration with hot EtOH gave 18.8 g (90%) of product as a white solid, mp 198°-200° C.; 1H NMR (DMSO-d6) δ 2.20 (s, 3 H), 4.46 (s, 2 H), 7.12 (dd, J=7.8 Hz, 1.5 Hz, 1 H), 7.25 (dd, J=7.8, 1.5 Hz, 1 H), 7.82 (m, 1 H), 8.41 (m, 2 H), 8.78 (s, 1 H), 10.26 (s, 1 H). To a stirred, cooled the mixture was concentrated filtered to give a brown solid

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