Phosphorus oxychloride → Isoquinoline, 1-chloro-

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69.3 g of isoquinoline N-oxide (448 mmol) manufactured by Tokyo Chemical Industry Co., Ltd. and 225 ml of chloroform were introduced into a 1 L-three-neck flask dissolved therein. Then, 219.6 g (1,432 mmol) of phosphorous oxychloride was slowly added dropwise therein and stirred under ice-cooling while maintaining the inner temperature at 15 to 20° C. Thereafter, the mixture was heated and stirred under reflux for 3 hours. The reaction product was left to cool to room temperature, and the resulting product was poured into ice water. The mixture was extracted with ethyl acetate, and the organic layer was washed with water until it was neutral. The solvent was then dried under reduced pressure. The residue was purified using silica gel column chromatography (eluent: chloroform/hexane: 5/1) to yield 35.5 g of 1-chloroisoquinoline white crystals (44.9% yield).

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