Ammonium Hydroxide → 4,5-DiaMino-2-fluorobenzonitrile

To a solution of 2,4-difluoro-5-nitrobenzonitrile (CAS #: 67152-20-9) (5.0 g, 27.2 mmol) in EtOH (100 mL) was added NH4OH (100 mL) slowly at room temperature. The mixture was stirred for 30 min, then concentrated under reduced pressure to about 100 mL. The yellow product was filtered and washed with water, and then dried. To a solution of the residue (3.96 g, 22 mmol) in EtOAc (150 mL) and acetic acid (25 mL) was added zinc (14.3 g, 219 mmol). The mixture was stirred at room temperature for 2 hour. The reaction mixture was diluted with EtOAc and filtered through a pad of Celite®. The Celite® pad was washed with EtOAc. The filtrate was concentrated, and the residue was dissolved in MeOH (50 mL) and NH4OH (100 mL). The mixture was then concentrated to around 100 mL and the mixture was left standing at room temperature overnight. The precipitate was filtered and washed with water, and then dried to give the title compound. MS (ESI+) m/z 152.1 (M+H).

1. concentrationconcentrated under reduced pressure to about 100 mL
2. filtrationThe yellow product was filtered
3. washwashed with water
4. customdried
5. stirringThe mixture was stirred at room temperature for 2 hour
6. filtrationfiltered through a pad of Celite®
7. washThe Celite® pad was washed with EtOAc
8. concentrationThe filtrate was concentrated
9. dissolutionthe residue was dissolved in MeOH (50 mL)
10. concentrationThe mixture was then concentrated to around 100 mL
11. waitthe mixture was left
12. waitstanding at room temperature overnight
13. filtrationThe precipitate was filtered
14. washwashed with water
15. customdried

ORD record

ord-8b7e22ab0ba64a9fac733148b785fe02

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056874B2