Stannous chloride dihydrate → 4-amino-2-fluoro-N,N-dimethylbenzamide

HRID 517430Notes

Reaction equation

[F:1][C:2]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].O.O.Cl[Sn]Cl>CCO>[NH2:13][C:11]1[CH:10]=[CH:9][C:3]([C:4]([N:6]([CH3:8])[CH3:7])=[O:5])=[C:2]([F:1])[CH:12]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a 50 mL round bottom flask was added 2-fluoro-N,N-dimethyl-4-nitro benzamide (2.8 g, 0.0132 mol) and EtOH (20 mL). To the same flask, SnCl2.2H2O (11.9 g, 0.0528 mol) was added and the reaction mixture was maintained at 85° C. for 2 h. The reaction mass was cooled to room temperature and the volatiles were evaporated under reduced pressure. The residue was dissolved in water and ethyl acetate. Aqueous saturated sodium bicarbonate was added to adjust to a pH of 7.0. The reaction mixture was filtered through a pad of Celite® reagent and washed with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain the title compound [2.5 g, 100%]. 1H NMR (300 MHz, CDCl3): δ 7.21 (t, J=7.8 Hz, 1H), 6.46 (dd, J′=8.4 Hz, J″=2.4 Hz, 1H), 6.34 (d, J′=11.4 Hz, J″=1.8 Hz, 1H), 3.95 (brs, 2H), 3.08 (s, 3H), 2.95 (d, J=1.8 Hz, 3H); LC-MS (ESI): Calculated mass: 182.1; Observed mass: 183.1 (RT: 0.17 min).

Workup

temperatureThe reaction mass was cooled to room temperature
customthe volatiles were evaporated under reduced pressure
dissolutionThe residue was dissolved in water
additionAqueous saturated sodium bicarbonate was added
filtrationThe reaction mixture was filtered through a pad of Celite® reagent
washwashed with ethyl acetate
customThe organic layer was separated
dry with materialdried over anhydrous sodium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-2183433b774a4afc9ec985753a1e666f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115092B2

Reaction notes

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