Hydrochloric Acid → HCID 43330295, compound

Participants

Reaction Steps

2,6-Dichloro-3-nitropyridine (II-1, 193 mg, 1 mmol) and p-cyanophenylamine (III-1, 236 mg, 2 mmol) were dissolved in N,N-dimethylformamide (DMF, 3 mL). While cooling in ice bath, potassium t-butoxide (224 mg, 2 mmol) was added in batch, followed by reacting at room temperature for 2 h. The reaction solution was poured into ice water, and adjusted with diluted HCl to a pH of 5-6, followed by stirring for 30 min, to precipitate a solid. The solid was filtered out, washed with water until neutral, dried, and separated via a silica gel column (dichloromethane as eluant), to obtain compound IV-1 (186 mg, 68%), a pale yellow solid, mp 175-178° C. 1H NMR (CDCl3) δ 10.47 (1H, br s, NH), 8.53 (1H, d, J=8.4 Hz, ArH-4), 7.86 (2H, d, J=8.8 Hz, ArH-2′, 6′), 7.70 (2H, d, J=8.8 Hz, ArH-3′, 5′), 6.96 (1H, d, J=8.4 Hz, ArH-5); MS (m/z): 275 (M+).

Provenance & Evidence