Sodium Hydroxide → HCID 21878493, compound

Participants

Reaction Steps

To 5 mL of ethanol was added [2-(1-Methyl-pyrrolidin-2-yl)-ethyl]-(5-nitro-benzothiazol-2-yl)-amine (Example 25(a), 177.4 mg, 0.577 mmol) and tin(II) chloride dihyrdate (948 mg, 5 eq.). The resulting solution was heated at reflux for 4 hours. After cooling to room temperature, the mixture was poured onto 100 mL of a 1.5 M NaOH solution. The mixture was extracted using ethyl acetate (3×100 mL). The combined organic fractions were dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel using 10% 2M ammonia/methanol in dichloromethane (98.4 mg, 62%). 1H NMR (CDCl3) δ: 7.32 (d, 1H, J=8.5 Hz), 6.91 (d, 1H, J=1.9 Hz), 6.49 (dd, 1H, J=1.9, 8.5 Hz), 3.67 (br s, NH2), 3.51 (m, 2H), 3.13–3.09 (m, 1H), 2.36 (s, 4H), 2.19 (m, 1H), 1.93–1.68 (m, 6H).

Provenance & Evidence