Methyl acetoacetate → HCID 178434117, compound

Participants

Reaction Conditions

Reaction Steps

Commercially available Quinoline N-oxide (Aldrich) (145 mg, 1 mmol) and methyl acetoacetate (0.1 mL, 1 mmol) was dissolved in acetic anhydride (2 mL) and heated at 90° C. for 1-2 hrs. The reaction mixture was cooled to room temperature and concentrated in vacuo, and the residue treated with ether. The resulting precipitate was filtered and dried in vacuo. Then, the crude material was dissolved in a mixture of ethanol and acetic acid (10:1, 2 mL) and treated with hydrazine (0.03 mL, 1 mmol). The mixture was stirred at ambient temperature for 18 hrs, and the resulting solid filtered and washed with a minimum amount of ethanol. 1H NMR (400 MHz, DMSO-D6) δ ppm 2.49 (s, 3H), 7.43-7.54 (m, 1H) 7.71 (t, J=7.33 Hz, 2H) 7.89 (d, J=7.83 Hz, 2H) 8.30 (d, J=8.34 Hz, 1H) 11.14 (s, 1H) 11.88 (s, 1H); ESI-MS: m/z calc'd for C13H11N3O 225.09. found 226.2 (M+H)+.

Provenance & Evidence