Sodium Hydroxide → HCID 66875319, compound

A pressure vial containing a mixture of 4-chloro-5-phenoxy-2H-pyridazin-3-one (1.76 g, 7.90 mmol), water (29.6 mL), and a 2N aqueous sodium hydroxide solution (4.26 mL) was treated with 10% palladium on carbon (174 mg, 10% weight of 4-chloro-5-phenoxy-2H-pyridazin-3-one). The reaction was then pressurized with hydrogen (50 psi), where it shook for 24 h. The resulting reaction mixture was diluted with methylene chloride (100 mL) and water (100 mL), filtered through a pad of diatomaceous earth, and rinsed. The layers were separated, and the organics were concentrated in vacuo. The aqueous layer was then acidified to pH 1-2 with a 2N aqueous hydrochloric acid solution. The resulting mixture was extracted with 90/10 methylene chloride/methanol (3×100 mL). These organics were combined, dried over sodium sulfate, filtered, rinsed, and concentrated in vacuo to afford 5-phenoxy-2H-pyridazin-3-one (1.44 g, 96%) as a white solid; ES+-HRMS m/e calcd for C10H8N2O2 [M+H+] 189.0659, found 189.0658.

1. additionA pressure vial containing
2. customThe resulting reaction mixture
3. filtrationfiltered through a pad of diatomaceous earth
4. washrinsed
5. customThe layers were separated
6. concentrationthe organics were concentrated in vacuo
7. extractionThe resulting mixture was extracted with 90/10 methylene chloride/methanol (3×100 mL)
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. washrinsed
11. concentrationconcentrated in vacuo

ORD record

ord-4e00df43f7b748d9b588b8a1261e99d9

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258134B2