4-Amino-3,5-xylenol

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:

Conditions: temp:77.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2,4-dichloronitrobenzene (3.0 g) in N,N-dimethylacetamide (30 ml) was added a 40% aqueous solution of methylamine (4.9 g) at room temperature, and the resulting mixture was stirred at 75-80° C. for 1.5 hours. To the reaction mixture were added 4-amino-3,5-dimethylphenol (2.2 g), potassium t-butoxide (3.5 g), and N,N-dimethylacetamide (15 ml), and the resulting mixture was stirred at the same temperature for 3 hours. After stirring, water (60 ml) was added to the reaction mixture, and the resulting mixture was cooled gradually to room temperature. The crystalline solid precipitated was collected by filtration and dried in vacuo to afford the title compound (3.0 g, yield: 67%) as a yellow crystalline solid. the resulting mixture was stirred at the same temperature for 3 hours After stirring the resulting mixture was cooled gradually to room temperature The crystalline solid precipitated was collected by filtration dried in vacuo

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

Procedure: To a solution of N-(5-chloro-2-nitrophenyl)-N-methylamine (8.00 g) in N,N-dimethylacetamide (112 ml) was added 2,6-di-t-butyl-4-methylphenol (0.24 g). Furthermore, to the resulting mixture were added 4-amino-3,5-dimethylphenol (6.47 g) and potassium t-butoxide (5.29 g) with stirring, and the resulting mixture was stirred at 60° C. for 30 minutes. After stirring, water (4 ml) was added to the reaction mixture, and furthermore water (120 ml) was added dropwise over a 2-hour interval, and then the resulting mixture was cooled gradually to room temperature. The crystalline solid precipitated was collected by filtration, washed with water (80 ml) and dried in vacuo to afford the title compound (11.45 g, yield: 93%) as a yellow crystalline solid. the resulting mixture was stirred at 60° C. for 30 minutes After stirring was added dropwise over a 2-hour interval The crystalline solid precipitated was collected by filtration washed with water (80 ml) dried in vacuo

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

Procedure: To a solution of N-(5-chloro-2-nitrophenyl)-N-methylamine (4.0 g) in N,N-dimethylacetamide (56 ml) were added 4-amino-3,5-dimethylphenol (2.9 g) and potassium t-butoxide (2.9 g) with stirring under ice-cooling, and the resulting mixture was stirred at 75-80° C. for 1 hour. After stirring, water (74 ml) was added to the reaction mixture, and the resulting mixture was cooled gradually to room temperature. The crystals precipitated were collected by filtration and dried in vacuo to afford the title compound (4.9 g, yield: 80%) as a yellow crystalline solid. cooling the resulting mixture was stirred at 75-80° C. for 1 hour After stirring The crystals precipitated were collected by filtration dried in vacuo

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

Procedure: To a suspension of anhydrous N,N-dimethylformaide (30 ml) containing sodium hydride (0.35 g, 55% (w/w)) was added 4-amino-3,5-dimethylphenol (1.10 g) and the mixture was stirred at room temperature for 15 minutes. To the mixture was added in limited amounts t-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate (2.29 g) and the mixture was stirred at 120° C. for 1 hour. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The extract was dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=1:3 as the eluant to afford the desired compound (2.27 g, Rf=0.24: thin layer chromatography on a silica gel plate using ethyl acetate:n-hexane=1:3 as the eluant). To a suspension of anhydrous N,N-dimethylformaide (30 ml) the mixture was stirred at 120° C. for 1 hour The reaction mixture was concentrated partitioned between ethyl acetate and water The extract was dried over anhydrous sodium sulfate concentrated The residue was chromatographed on a silica gel column

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

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