Sodium Chloride → N'-(5-Amino-2-cyanophenyl)-N,N-dimethylformimidamide

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Reaction Conditions

Reaction Steps

N′-(2-Cyano-5-nitrophenyl)-N,N-dimethylformimidamide (1.0 g, 4.58 mmol) is dissolved in 100 mL of tetrahydrofuran, cooled to 0° C. and admixed with titanium trichloride solution (69 mL of a 15% solution in 10% aqueous HCl). Then, the batch is stirred at room temperature for 4 hours and adjusted at 0° C. to pH 9 with 2N aqueous sodium hydroxide solution. The mixture is diluted with water and ethyl acetate. The aqueous phase is saturated with sodium chloride and stirred out three times with ethyl acetate. The combined organic phases are dried over sodium sulphate. Removal of the solvent and also chromatographic purification (silica gel, n-hexane/ethyl acetate:→100% ethyl acetate) gives the desired product in 73% yield (630 mg).

Provenance & Evidence