Ammonia → 6-Chloro-3-methyl-5-nitroisoquinoline

To a solution of 6-chloro-3-methylisoquinoline (10.0 g, 57.5 mmol) in concentrated H2SO4 (100 mL) was added dropwise during 10 min. a solution of KNO3 (6.05 g, 60 mmol) in concentrated H2SO4 (50 mL) at 5° C. Care was taken that the temperature of the reaction mixture did not rise above 10° C. The reaction mixture was stirred for 3 h at room temperature, poured onto ice (200 g) and rendered basic (pH=10) with a 33% aqueous ammonia solution. A dark yellow precipitate was formed, which was filtered off, thoroughly rinsed with water and taken up in dichloromethane. The organic phase was washed with water and brine, dried over Na2SO4, filtered and dried in vacuo to afford a pale brown solid. Re-crystallization from dichloromethane/pentane afforded the title compound as pale brown crystals (9.2, 41.4 mmol, 72%). MS (ES+): 223 (M(C10H735ClN2O2)+H)+.

1. customdid not rise above 10° C
2. additionpoured onto ice (200 g)
3. customA dark yellow precipitate was formed
4. filtrationwhich was filtered off
5. washthoroughly rinsed with water
6. washThe organic phase was washed with water and brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. customdried in vacuo
10. customto afford a pale brown solid

ORD-Eintrag

ord-633b1b3260484b05b15837193fe8447c

Quelldatensatz

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08426440B2