1,2-Dichloroethane → HCID 87106358, compound

Participants

Reaction Steps

To a suspension of 250 mg (1.37 mmol) of (6-nitropyridin-2-yl) acetic acid in 6 mL of dichloromethane was added DIEA (0.72 mL, 4.12 mmol) which resulted in some exotherming (+5° C.) and the suspension becoming a solution. After 2 min cooling, HOBt (263 mg, 1.72 mmol), N,O-dimethylhydroxylamine HCl (167 mg, 1.72 mmol) was added to the solution followed by EDC (329 mg, 1.72 mmol) and the resulting mixture stirred at room temperature overnight under nitrogen atmosphere. The solution was transferred to a separatory funnel and washed with 1 M HCl which caused an emulsion. Methanol was added to break up the emulsion and the aqueous was partitioned off. The organics were dried over sodium sulfate, filtered and concentrated under vacuum. Purification via preparative TLC plate (2×1000 μM) eluting with 50% ethyl acetatehexane afforded the title compound (236 mg, 76%) as a white solid. LC-MS: C9H11N3O4 calculated 225.20 found m/z (ES) 226 (MH)+. 1HNMR (500 MHz, DMSO) δ:8.56 (d, J=2.0 Hz, 1H), 8.25 (d, J=8.4 Hz, 1H), 8.04 (dd, J=2.0, 8.3 Hz, 1H), 4.02 (br s, 2H), 3.88 (s, 3H), 3.07 (s, 3H).

Provenance & Evidence