Nitric Acid → 2,2,2-Trichloro-1-(1-methyl-4-nitro-1H-pyrrol-2-yl)ethan-1-one

Temperature

-20 °C

2.12 g (9.34 mmol) of 1-methyl-2-trichloroacetyl-1H-pyrrole are dissolved in 9.5 ml of acetic anhydride and cooled to −20° C., and 0.43 ml (9.34 mmol) of nitric acid is added. The mixture is slowly warmed to RT and stirred at RT for 1 h. The reaction mixture is poured into 95 g of ice and stirred vigorously for 2.5 h (initially oily deposit then crystallization). The precipitate is filtered off with suction, triturated with 20 ml of methanol, filtered and dried under reduced pressure overnight. To remove the regioisomers, which are also formed, the product is triturated with 10 ml of acetic acid/water 1:1 for 2 h, and the solid is filtered off with suction and dried under reduced pressure. This gives a solid.

1. temperatureThe mixture is slowly warmed to RT
2. stirringstirred vigorously for 2.5 h (initially oily deposit
3. customcrystallization)
4. filtrationThe precipitate is filtered off with suction
5. customtriturated with 20 ml of methanol
6. filtrationfiltered
7. customdried under reduced pressure overnight
8. customTo remove the regioisomers, which
9. customare also formed
10. customthe product is triturated with 10 ml of acetic acid/water 1:1 for 2 h
11. filtrationthe solid is filtered off with suction
12. customdried under reduced pressure
13. customThis gives a solid

ORD record

ord-67345c5b026340a8b51cf540126f648a

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410090B2