Methanol → HCID 9965471, compound

Temperature

50 °C

The ester from Step 4 (1.3 g, 4.4 mmol) and 2.5 N sodium hydroxide solution (3.5 mL, 9 mmol) were mixed in tetrahydrofuran (25 mL), methanol (10 mL), and water (25 mL). The mixture was heated at 50° C. for 4 hours, allowed to cool to room temperature, and was concentrated in vacuo to remove the tetrahydrofuran and methanol. The resulting aqueous solution was washed with diethyl ether (2×100 mL). The aqueous phase was acidified with 3 N HCl causing the precipitation of a yellow solid (1.1 g). The solid was triturated with ethanol-acetone and collected by vacuum filtration providing the title compound as a yellow solid (276 mg, 23%): mp 287.4–288.4° C. 1H NMR (acetone-d6/300 MHz) 11.50 (br s, 1H), 8.03 (s, 1H), 7.83 (s, 1H), 7.75 (s, 1H), 7.28 (br s, 1H), 5.42–5.30 (m, 1H). Anal. Calc'd for C10H6N2O2F3Cl: C, 43.11; H, 2.17; N, 10.05 Found: C, 42.88; H, 2.03; N, 10.06.

1. temperatureto cool to room temperature
2. concentrationwas concentrated in vacuo
3. customto remove the tetrahydrofuran and methanol
4. washThe resulting aqueous solution was washed with diethyl ether (2×100 mL)
5. customthe precipitation of a yellow solid (1.1 g)
6. customThe solid was triturated with ethanol-acetone
7. filtrationcollected by vacuum filtration

ORD record

ord-93d7d5f620954d3b848f968af0a82bd3

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07138411B2