Ammonia → HCID 10399247, compound

Participants

Reaction Steps

To an ice cooled solution of the compound of step 9a (286 mg, 1.08 mmol) in absolute ethanol (4 mL), was added a hydrogen chloride saturated ethanol solution (4 mL), under nitrogen. The reaction mixture was stirred 18 hours while gradually warming to room temperature. The reaction mixture was then concentrated in vacuo, the product dissolved in absolute ethanol and triturated with diethyl ether. Two recrystallizations from ethanol and diethyl ether yielded pure product in 81% yield as a white powder (174 mg, 87 mmol). MS (DCI/NH3) m/e 165 (M+H)+, 182 (M+NH4)+. 1NMR (D2O, 300 MHz) δ: 8.60-8.59 (d, J=2.9 Hz, 1H), 8.48-8.46 (d, J=5.8 Hz, 1H), 8.25-8.21 (ddd, J=9.0 Hz, J=2.6 Hz, J=1.1 Hz, 1H), 5.05-4.97 (m, 1H), 4.59-4.57 (d, J=4.0 Hz, 2H), 4.22-4.05 (m, 2H), 2.77-2.67 (dd, J=16.9 Hz, J=8.45 Hz, 2H). Anal. calcd. for C9H12N2O.2.7 HCl.0.2 H2O: C, 40.60; H, 5.71; N, 10.52. Found: C, 40.75; H, 5.76; N, 10.51.

Provenance & Evidence