Hydrochloric Acid → 2-chloro-N1,N1-dihexylbenzene-1,4-diamine

Temperature

65 °C

A mixture of concentrated hydrochloric acid (1.0 mL), water (50 mL) and iron powder (5.58 g, 100 mmol) was stirred at 65° C. for 15 min. The aqueous layer of the mixture was poured out, and a solution of 2-chloro-N,N-dihexyl-4-nitroaniline (3.41 g, 10 mmol) in MeOH (100 mL) was added to the above processed iron powder. The mixture was acidified to pH 3 with hydrochloric acid and stirred at 65° C. for 45 min. The mixture was then cooled to rt, adjusted to pH 10 with Et3N and filtered. The filtrate was concentrated in vacuo and the residue was dissolved in 150 mL of DCM. The solution was washed with water (100 mL×3) and brine (100 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as colorless oil (3.00 g, 97%).

1. additionThe aqueous layer of the mixture was poured out
2. stirringstirred at 65° C. for 45 min
3. temperatureThe mixture was then cooled to rt
4. filtrationfiltered
5. concentrationThe filtrate was concentrated in vacuo
6. dissolutionthe residue was dissolved in 150 mL of DCM
7. washThe solution was washed with water (100 mL×3) and brine (100 mL)
8. dry with materialdried over anhydrous Na2SO4
9. concentrationconcentrated in vacuo

ORD record

ord-e4ba8e6bdba4456c8565c100d1d7919f

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434695B2