6,7-dimethylnaphthalene-1,4-dione

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

Procedure: To a warm solution of 6,7-dimethyl-1,4-naphthoquinone (1.08g; 0.058 mole) in ethanol (20ml) was added aniline (0.5ml) and the red solution refluxed for 1 hr. on a steam bath. After standing overnight the red crystalline anilino derivative was filtered off and recrystallised from acetic acid; water to give 0.54g (34%) of material of m.p. 208°-210° C. (Found C, 78.02; H, 5,47; N, 4.88; C18H15NO2 requires; C, 77.96; H, 5.45; N, 5.05%). the red solution refluxed for 1 hr the red crystalline anilino derivative was filtered off recrystallised from acetic acid

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

Procedure: To a warm solution of 6,7-dimethyl-1,4-naphthoquinone (1.08g; 0.058 mole) in ethanol (20ml) was added aniline (0.5ml) and the red solution refluxed for 1 hr. on a steam bath. After standing overnight the red crystalline anilino derivative was filtered off and recrystallized from acetic acid; water to give 0.54g (34%) of material of m.p. 208°-210° C. (Found; C, 78.02; H, 5.47; N, 4.88; C18H15NO2 requires; C, 77.96; H, 5.45; N, 5.05%). the red solution refluxed for 1 hr the red crystalline anilino derivative was filtered off recrystallized from acetic acid

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

Procedure: A solution of 6,7-dimethyl naphtho-1,4-quinone (20.0 g.; 0.107 mole) in glacial acetic acid (250 ml) was stirred during the dropwise addition of bromine (5.6 ml; 17.2 g; 0.107 mole) in acetic acid (10 ml.) at 15° C and allowed to stir at this temperature for a further 2 hours. Anhydrous sodium acetate (20 g) was added and the mixture stirred at 100° C for 11/2 hours after an initial half hour period at room temperature; cooled, poured into water (2.5 l) and the yellow bromo product filtered off. It had m.p. (ethanol, chloroform) 156°-159° C. (Found; C, 53.47; H, 3.39; Br. 30.23; C12H9BrO2 requires; C, 54.36; H, 3.42; Br, 30.14%). the mixture stirred at 100° C for 11/2 hours after an initial half hour period at room temperature cooled the yellow bromo product filtered off (ethanol, chloroform) 156°-159° C. (Found; C, 53.47; H, 3.39; Br. 30.23; C12H9BrO2 requires; C, 54.36; H, 3.42; Br, 30.14%)

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

Procedure: A solution of 6,7-dimethyl naphtho-1,4-quinone (20.0 g.; 0.107 mole) in glacial acetic acid (250 ml) was stirred during the dropwise addition of bromine (5.6 ml; 17.2 g; 0.107 mole) in acetic acid (10 ml.) at 15° C and allowed to stir at this temperature for a further 2 hours. Anhydrous sodium acetate (20 g) was added and the mixture stirred at 100° C for 11/2 hours after an initial half hour period at room temperature; cooled, poured into water (2.5 l) and the yellow bromo product filtered off. It had m.p. (ethanol, chloroform) 156°-159° C. (Found; C, 53.47; H, 3.39; Br. 30.23; C12H9BrO2 requires; C, 54.36; H, 3.42; Br, 30.14%). the mixture stirred at 100° C for 11/2 hours after an initial half hour period at room temperature cooled the yellow bromo product filtered off (ethanol, chloroform) 156°-159° C. (Found; C, 53.47; H, 3.39; Br. 30.23; C12H9BrO2 requires; C, 54.36; H, 3.42; Br, 30.14%)

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

Procedure: A solution of 6,7-dimethyl naphtho-1,4-quinone (20.0 g.; 0.107 mole) in glacial acetic acid (250 ml) was stirred during the dropwise addition of bromine (5.6 ml; 17.2 g; 0.107 mole) in acetic acid (10 ml.) at 15° C. and allowed to stir at this temperature for a further 2 hours. Anhydrous sodium acetate (20 g) was added and the mixture stirred at 100° C. for 11/2 hours after an initial half hour period at room temperature; cooled, poured into water (2.5 l) and the yellow bromo product filtered off. It had m.p. (ethanol, chloroform) 156°-159° C. (Found; C, 53.47; H, 3.39; Br, 30.23; C12H9BrO2 requires; C, 54.36; H, 3.42; Br, 30.14%): the mixture stirred at 100° C. for 11/2 hours after an initial half hour period at room temperature cooled the yellow bromo product filtered off (ethanol, chloroform) 156°-159° C. (Found; C, 53.47; H, 3.39; Br, 30.23; C12H9BrO2 requires; C, 54.36; H, 3.42; Br, 30.14%)

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

Procedure: To a warm solution of 6,7-dimethyl-1,4-naphthoquinone (1.08g; 0.058 mole) in ethanol (20ml) was added aniline (0.5ml) and the red solution refluxed for 1 hr. on a steam bath. After standing overnight the red crystalline anilino derivative was filtered off and recrystallised from acetic acid; water to give 0.54g (34%) of material of m.p. 208°-210° C. (Found C, 78.02; H, 5,47; N, 4.88; C18H15NO2 requires; C, 77.96; H, 5.45; N, 5.05%). the red solution refluxed for 1 hr the red crystalline anilino derivative was filtered off recrystallised from acetic acid

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

Procedure: To a warm solution of 6,7-dimethyl-1,4-naphthoquinone (1.08g; 0.058 mole) in ethanol (20ml) was added aniline (0.5ml) and the red solution refluxed for 1 hr. on a steam bath. After standing overnight the red crystalline anilino derivative was filtered off and recrystallised from acetic acid; water to give 0.54g (34%) of material of m.p. 208°-210° C. (Found C, 78.02; H, 5,47; N, 4.88; C18H15NO2 requires; C, 77.96; H, 5.45; N, 5.05%). the red solution refluxed for 1 hr the red crystalline anilino derivative was filtered off recrystallised from acetic acid

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

Procedure: To a warm solution of 6,7-dimethyl-1,4-naphthoquinone (1.08g; 0.058 mole) in ethanol (20ml) was added aniline (0.5ml) and the red solution refluxed for 1 hr. on a steam bath. After standing overnight the red crystalline anilino derivative was filtered off and recrystallized from acetic acid; water to give 0.54g (34%) of material of m.p. 208°-210° C. (Found; C, 78.02; H, 5.47; N, 4.88; C18H15NO2 requires; C, 77.96; H, 5.45; N, 5.05%). the red solution refluxed for 1 hr the red crystalline anilino derivative was filtered off recrystallized from acetic acid

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

Procedure: A solution of 6,7-dimethyl naphtho-1,4-quinone (20.0 g.; 0.107 mole) in glacial acetic acid (250 ml) was stirred during the dropwise addition of bromine (5.6 ml; 17.2 g; 0.107 mole) in acetic acid (10 ml.) at 15° C and allowed to stir at this temperature for a further 2 hours. Anhydrous sodium acetate (20 g) was added and the mixture stirred at 100° C for 11/2 hours after an initial half hour period at room temperature; cooled, poured into water (2.5 l) and the yellow bromo product filtered off. It had m.p. (ethanol, chloroform) 156°-159° C. (Found; C, 53.47; H, 3.39; Br. 30.23; C12H9BrO2 requires; C, 54.36; H, 3.42; Br, 30.14%). the mixture stirred at 100° C for 11/2 hours after an initial half hour period at room temperature cooled the yellow bromo product filtered off (ethanol, chloroform) 156°-159° C. (Found; C, 53.47; H, 3.39; Br. 30.23; C12H9BrO2 requires; C, 54.36; H, 3.42; Br, 30.14%)

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

Procedure: A solution of 6,7-dimethyl naphtho-1,4-quinone (20.0 g.; 0.107 mole) in glacial acetic acid (250 ml) was stirred during the dropwise addition of bromine (5.6 ml; 17.2 g; 0.107 mole) in acetic acid (10 ml.) at 15° C. and allowed to stir at this temperature for a further 2 hours. Anhydrous sodium acetate (20 g) was added and the mixture stirred at 100° C. for 11/2 hours after an initial half hour period at room temperature; cooled, poured into water (2.5 l) and the yellow bromo product filtered off. It had m.p. (ethanol, chloroform) 156°-159° C. (Found; C, 53.47; H, 3.39; Br, 30.23; C12H9BrO2 requires; C, 54.36; H, 3.42; Br, 30.14%): the mixture stirred at 100° C. for 11/2 hours after an initial half hour period at room temperature cooled the yellow bromo product filtered off (ethanol, chloroform) 156°-159° C. (Found; C, 53.47; H, 3.39; Br, 30.23; C12H9BrO2 requires; C, 54.36; H, 3.42; Br, 30.14%)

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

Procedure: To a warm solution of 6,7-dimethyl-1,4-naphthoquinone (1.08g; 0.058 mole) in ethanol (20ml) was added aniline (0.5ml) and the red solution refluxed for 1 hr. on a steam bath. After standing overnight the red crystalline anilino derivative was filtered off and recrystallised from acetic acid; water to give 0.54g (34%) of material of m.p. 208°-210° C. (Found C, 78.02; H, 5,47; N, 4.88; C18H15NO2 requires; C, 77.96; H, 5.45; N, 5.05%). the red solution refluxed for 1 hr the red crystalline anilino derivative was filtered off recrystallised from acetic acid