Acetone → HCID 922186, compound

To a mixture of 3-bromo-4-methylbenzohydrazide (2.0 g, 8.72 mmol, 1.0 eq) and acetone (10 mL, 172 mmol, 21 eq) in hexane (10 mL), was added molecular sieves (500 mg) followed by trifluoroacetic acid (2 mL) and the resulting mixture was refluxed for 3 h. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated under vacuum and the residue was taken in ethyl acetae (100 mL), washed with water (50 mL), aqueous saturated sodium bicarbonate solution (50 mL), brine (50 mL), dried (Na2SO4) and filtered. The filtrate was concentrated under reduced pressure to afford the 2.10 g of the 3-bromo-4-methyl-N′-(propan-2-ylidene)benzohydrazide. 1HNMR (400 MHz, DMSO-d6) δ 10.51 (s, 1H, D2O exchangeable), 8.02 (s, 1H), 7.75 (dd, J=1.0, 8.0 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H), 2.40 (s, 3H), 2.01 (s, 3H), 1.94 (s, 3H); ESI-MS (m/z) 269, 271 [(MH)+, Br79,81].

1. additionwas added molecular sieves (500 mg)
2. temperaturethe resulting mixture was refluxed for 3 h
3. filtrationfiltered
4. concentrationThe filtrate was concentrated under vacuum
5. washwashed with water (50 mL), aqueous saturated sodium bicarbonate solution (50 mL), brine (50 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-05203101b8024d0686124e07028883b6

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169242B2