Chloroacetone → HCID 49871062, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,4-diamino-3-iodopyridine 22 (4.36 g, 18.6 mmol) in ethanol (100 mL) was added chloracetone (7.15 g, 77.3 mmol). The solution was stirred at 65° C. for 6 h. After cooling to room temperature, the solution was evaporated to dryness. The residue was diluted with water (75 mL) and the resulting solution made basic (pH=12-13) by the addition of a ammonium hydroxide solution. The solution was extracted with CH2Cl2 and the combinated extracts were dried (Na2SO4), filtered and evaporated under reduced pressure. The crude product was purified by chromatography using CH2Cl2/EtOAc (4/1, v/v) as eluent to afford compound 23 (3.30 g, yield: 65%); mp 185° C.; IR (KBr) 3454, 3431, 3355, 3093, 3026, 1646, 1499, 1463; 1H NMR (400 MHz, DMSO-d6) δ 2.19 (s, 3H), 5.68 (brs, 2H), 6.38 (d, 1H, J=7.1 Hz), 7.42 (s, 1H), 8.03 (d, 1H, J=7.1 Hz); 13C NMR (100 MHz, DMSO-d6) δ 14.1, 60.9, 103.8, 109.3, 126.0, 140.4, 145.6, 146.6. Anal. Calcd for C8H8IN3: C, 35.19; H, 2.95; N, 15.39. Found: C, 35.25; H, 2.92; N, 15.60.

Provenance & Evidence