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With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 100℃; for 24 h;
[0121] A mixture of 5-bromo-3,4-dihydro-2H-isoquinolin-l-one (4.3 g, 18.9 mmol) and 2,3-dicyano-5,6-dichloro-l,4-benzoquinone (8.6 g, 37.9 mmol) in 1,4-dioxane (76 mL) was stirred at 100 °C for 24 h. The reaction mixture was evaporated and the residue was taken up in ethyl acetate (500 mL) and washed with 10percent aqueous sodium hydroxide (2 x 500 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (4 x 300 mL). The combined organic layers were dried over sodium sulfate, evaporated and purified by flash chromatography eluting with dichloromethane: methanol (99: 1 -^96:4) to give the title compound (1.49 g, 6.65 mmol, 35percent) as a yellow solid. LCMS: 94percent, Rt 1.243, ESMS m/z 224 (M+H)+.
35%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 100℃; for 24 h;
-1. 5-Bromo-2H-isoquinolin-l-one. [00114] A mixture of 5-bromo-3,4-dihydro-2H-isoquinolin-l -one (Preparation 3-1, 4.3 g, 18.9 mmol) and 2,3-dicyano-5,6-dichloro-l,4-benzoquinone (8.6 g, 37.9 mmol) in 1,4-dioxane (76 mL) was stirred at 100 °C for 24 h. The reaction mixture was evaporated and the residue was taken up in ethyl acetate (500 mL) and washed with 10percent aqueous sodium hydroxide (2 x 500 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (4 x 300 mL). The combined organic layers were dried over sodium sulfate, evaporated and purified by flash chromatography eluting with dichloromethane:methanol (99: 1 -^96:4) to give the title compound (1.49 g, 6.65 mmol, 35percent) as a yellow solid. LCMS: 94percent, Rt 1.243, ESMS m/z 224 (M+H)+.
35%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 100℃; for 24 h;
[001081 A mixture of 5-bromo-3,4-dihydro-2H-isoquinolin-1-one (Preparation 3-1, 4.3 g, 18.9 mmol) and 2,3-dicyano-5,6-dichloro-1,4-benzoquinone (8.6 g, 37.9 mmol) in 1,4-dioxane (76 mL) was stirred at 100 °C for 24 h. The reaction mixture was evaporated and the residue was taken up in ethyl acetate (500 mL) and washed with 10percent aqueous sodium hydroxide (2 x 500 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (4 x 300 mL). The combined organic layers were dried over sodium sulfate, evaporated and purified by flash chromatography eluting with dichloromethane:methanol (99:1 -96:4) to give the title compound (1.49 g, 6.65 mmol, 35percent) as a yellow solid. LCMS: 94percent, Rt 1.243, ESMS m/z 224 (M+H).
Stage #1: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 0.5 h; Stage #2: for 1 h; Reflux
Commercially available 5-bromoisoquinoline (4.85 g, 23.3 mmol) was dissolved in dichloromethane (78 mL), and m-CPBA (9.28 g, 35.0 mmol) was added. The mixture was stirred at room temperature for 0.5 hours. The reaction mixture was diluted by adding chloroform, and washed with a saturated sodium bicarbonate aqueous solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in acetic anhydride (78.0 mL), and stirred for 1 hour under reflux. A 2.0 mol/L sodium hydroxide aqueous solution (156 mL) was added to the residue obtained by concentrating the reaction mixture under reduced pressure, and the mixture was stirred for 2 hours under reflux. The reaction mixture was cooled to room temperature, and neutralized with a 2.0 mol/L hydrochloric acid aqueous solution. The precipitated crystals were collected by filtration, and dried under reduced pressure to give 5-bromoisoquinolin-1(2H)-one (2.28 g, 10.1 mmol, 43percent).
Reference：
[1] Patent: EP2708540, 2014, A1, . Location in patent: Paragraph 0122
[2] Patent: US2014/302987, 2014, A1,
[3] Chemistry - A European Journal, 2015, vol. 21, # 18, p. 6906 - 6912
3
[ 245677-36-5 ]
[ 190777-77-6 ]
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2031 - 2036
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