Methyl acetoacetate → HCID 178434117, compound

Temperature

90 °C

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)+.

1. temperatureThe reaction mixture was cooled to room temperature
2. concentrationconcentrated in vacuo
3. additionthe residue treated with ether
4. filtrationThe resulting precipitate was filtered
5. customdried in vacuo
6. dissolutionThen, the crude material was dissolved in a mixture of ethanol and acetic acid (10:1, 2 mL)
7. filtrationthe resulting solid filtered
8. washwashed with a minimum amount of ethanol

ORD record

ord-0bfb37fe1b104d93adcd400a67ece17a

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07550598B2