Hydrazine hydrate (1:1) → HCID 178506369, compound

A solution of 0.137 g (0.48 mmol) of 3-(2-trifluoromethoxyphenyl)-benzamide in 1 mL of N,N-dimethylformamide dimethyl acetal was heated at 120° C. for 2 h at which time the reaction was concentrated in vacuo. To this material in 2.3 mL of acetic acid was added 0.028 g (0.55 mmol) of hydrazine hydrate and the reaction mixture was heated at 90° C. for 2 h. The reaction mixture was then concentrated and partitioned between EtOAc and saturated NaHCO3 solution. The organic fraction was washed with brine, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, 30:1, 9:1, 3:1 successively CH2Cl2: acetone) to give the title compound. 1H NMR (CD3OD) (δ, ppm): 8.32 (s, 1H), 8.06 (s, 1H), 7.98 (m, 1H), 7.50 (m, 3H), 7.39(m, 3H). Mass Spectrum (ESI) m/e (M+1): 306.1.

1. concentrationwas concentrated in vacuo
2. concentrationThe reaction mixture was then concentrated
3. custompartitioned between EtOAc and saturated NaHCO3 solution
4. washThe organic fraction was washed with brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationthe filtrate was concentrated
8. customThe residue was purified by chromatography (silica, 30:1, 9:1, 3:1 successively CH2Cl2

ORD record

ord-dcd35586fa5f450582e86994830366a0

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07459475B2