Hydrochloric Acid → N,2,6-Trimethylaniline hydrochloride

A suspension of 125.6 g. of 2,6-dimethylformanilide in 1100 ml. of dry tetrahydrofuran is cooled to 0° C. in ice-methanol. To this with constant stirring is added dropwise over a period of 3 hours 1125 ml. of 0.96 M BH3 in tetrahydrofuran. This is then allowed to warm gradually to room temperature and then heated slowly to reflux. Refluxing is maintained for 6 hours and then stirred at room temperature another 15 hours. The reaction mixture is then cooled in ice and acidified with 425 ml. of 6 N HCl. A white solid forms. The mixture is evaporated in vacuo and the water-solid slurry dissolved into 2 l. of water. The solution is made strongly alkaline (with cooling) with 50% NaOH and then extracted twice with ether (2 l.) The ether is then washed three times with 100 ml. portions of water and twice with 100 ml. portions of saturated sodium chloride solution. The ether is then dried over sodium sulfate, filtered, acidified with ethereal HCl while cooling. The white solid which forms is filtered, washed with ether and sucked dry. This is recrystallized from isopropanol:methanol to give N,2,6-trimethylaniline hydrochloride (m.p. 255-257 dec.)

1. additionA suspension of 125.6 g
2. additionis added dropwise over a period of 3 hours 1125 ml
3. temperatureheated slowly
4. temperatureto reflux
5. temperatureRefluxing
6. temperatureis maintained for 6 hours
7. stirringstirred at room temperature another 15 hours
8. temperatureThe reaction mixture is then cooled in ice
9. customThe mixture is evaporated in vacuo
10. dissolutionthe water-solid slurry dissolved into 2 l
11. temperature(with cooling) with 50% NaOH
12. extractionextracted twice with ether (2 l.) The ether
13. washis then washed three times with 100 ml
14. dry with materialThe ether is then dried over sodium sulfate
15. filtrationfiltered
16. temperaturewhile cooling
17. filtrationThe white solid which forms is filtered
18. washwashed with ether
19. customsucked dry
20. customThis is recrystallized from isopropanol

ORD record

ord-4b46a0becb654b13b9563eb11d502ac4

Source dataset

uspto-grants-1979_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04147804