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温度

0 °C

A 70° C. solution of sodium sulfide (3.17 g, 32.97 mmol) and sodium bicarbonate in water (7 mL) was added dropwise to suspension of 1,5-dinitro naphthalene (2.0 g, 9.16 mmol) in methanol (30 mL) at reflux and the resultant mixture was stirred for 5 min. The mixture was cooled to 0° C., quenched with ice and stirred for a further 10 min followed by acidification with concentrated hydrochloric acid. The resulting mixture was stirred for 30 min then washed with ethyl acetate (2×50 mL). The aqueous layer was basified with aqueous ammonia and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water (2×50 mL), brine (2×50 mL), dried over anhydrous sodium sulphate, filtrated and concentration in vacuo afforded of 5-nitronaphthalen-1-amine (710 mg, 42%) as a brown solid.

1. temperatureat reflux
2. customquenched with ice
3. stirringThe resulting mixture was stirred for 30 min
4. washthen washed with ethyl acetate (2×50 mL)
5. extractionextracted with ethyl acetate (2×100 mL)
6. washThe combined organic layers were washed with water (2×50 mL), brine (2×50 mL)
7. dry with materialdried over anhydrous sodium sulphate
8. filtrationfiltrated
9. concentrationconcentration in vacuo