Ammonium Chloride → HCID 21959409, compound

4-(2-tert-Butyl-5-nitrophenyl)-1-methylpyridinium (2.1 g, 7.8 mmol, Step C) was added to a 100 mL round-bottom flask and dissolved in a 10% H2O/EtOH mixture. To the flask iron dust (1.31 g, 23.4 mmol) and NH4Cl (460 mg, 8.6 mmol) were added. The flask was placed in a 100° C. sand bath and heated to reflux. After 2 h the solution was cooled to RT and filtered through a pad of Celite®. The resulting solution was concentrated in vacuo to a yellow solid and re-dissolved in MeOH (20 mL, anhydrous). The solution was cooled to 0° C. by placing it in an ice bath and slowly adding NaBH4 (450 mg, 11.7 mmol). After addition of the NaBH4, the solution was cooled to RT and stirred for 30 min. The solvent was concentrated in vacuo and the solid was re-dissolved in CH2Cl2 and filtered. The solution was again concentrated in vacuo to afford an amorphous clear yellow solid. MS (ES+): 245.2 (M+H)+. Calc'd for C16H24N2: 244.19.

1. customwas placed in a 100° C.
2. temperatureheated to reflux
3. filtrationfiltered through a pad of Celite®
4. concentrationThe resulting solution was concentrated in vacuo to a yellow solid
5. dissolutionre-dissolved in MeOH (20 mL, anhydrous)
6. temperatureThe solution was cooled to 0° C.
7. temperaturethe solution was cooled to RT
8. concentrationThe solvent was concentrated in vacuo
9. dissolutionthe solid was re-dissolved in CH2Cl2
10. filtrationfiltered
11. concentrationThe solution was again concentrated in vacuo
12. customto afford an amorphous clear yellow solid

ORD record

ord-d0fc080713ba46728dd119dfd5a12baf

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06995162B2