Triethylamine → N1-(2-chloro-3-nitroquinolin-4-yl)-2-methylpropane-1,2-diamine

Temperature

0 °C

Under a nitrogen atmosphere, triethylamine (6.6 mL, 47 mmol) was added slowly to a solution of 2,4-dichloro-3-nitroquinoline (10.0 g, 41.1 mmol) in anhydrous 1-methyl-2-pyrrolidinone (40 mL). The reaction mixture was cooled to 0° C. with an ice bath. A solution of 1,2-diamino-2-methylpropane (4.1 g, 47.3 mmol) in anhydrous 1-methyl-2-pyrrolidinone (5 mL) was added dropwise over a period of 15 minutes while maintaining the temperature of the reaction mixture below 4° C. After the addition was completed the ice bath was removed and the reaction mixture was allowed to stir at ambient temperature for 4 hours. The reaction mixture was slowly poured into vigorously stirred warm water (300 mL). The resulting suspension was stirred for 1 hour and then cooled to 13° C. by adding ice. The solid was isolated by filtration and then washed with cold water until the filtrate was clear to provide 12.1 g of N1-(2-chloro-3-nitroquinolin-4-yl)-2-methylpropane-1,2-diamine as a damp yellow solid.

1. temperaturewhile maintaining the temperature of the reaction mixture below 4° C
2. additionAfter the addition
3. customwas removed
4. additionThe reaction mixture was slowly poured
5. stirringinto vigorously stirred
6. temperaturewarm water (300 mL)
7. stirringThe resulting suspension was stirred for 1 hour
8. temperaturecooled to 13° C.
9. additionby adding ice
10. customThe solid was isolated by filtration
11. washwashed with cold water until the filtrate

ORD record

ord-0b3ecddf836747f0961dfc22a6015691

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846710B2