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

HRID 2092527Notes

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-0e017645975a40ed892e7aeefdd4ca57
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440662B2

Reaction notes

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