反应详情

温度

150 °C

A mixture of 2-methyl-3-nitroaniline (10 g), glycerin (20.57 g) and As2O5.xH2O (Baker, 88% As2O5, 8.5 g) is heated slowly to 150° C. in an open round-bottom flask, then stirred for 6 hrs at 150° C. The resulting mixture is cooled to room temperature and diluted with water (200 mL), then basified with ammonium hydroxide (28-30%, 100 mL). After about 10 minutes, the solution is acidified to pH=5 with glacial acetic acid and extracted with CH2Cl2 (3×200 mL). The combined extracts are washed with H2O (200 mL), sat. NaHCO3 (200 mL), then dried over MgSO4 and rotary evaporated. The crude quinoline is filtered through a short pad of silica gel, using CH2Cl2 as solvent. The filtrate is rotary evaporated and the residue recrystallized from hexane/CH2Cl2 to afford 8-methyl-7-nitroquinoline as a tan solid.

1. temperatureThe resulting mixture is cooled to room temperature
2. waitAfter about 10 minutes
3. extractionextracted with CH2Cl2 (3×200 mL)
4. washThe combined extracts are washed with H2O (200 mL), sat. NaHCO3 (200 mL)
5. dry with materialdried over MgSO4 and rotary evaporated
6. filtrationThe crude quinoline is filtered through a short pad of silica gel
7. customThe filtrate is rotary evaporated
8. customthe residue recrystallized from hexane/CH2Cl2