Toluene → 2-Methylphthalazin-1-one

Temperature

85 °C

To a suspension of 4-p-toluyl-phthalazin-1-(2H)-one [compound 2D] (2.36 g, 10 mMol) in toluene (50 mL) were added 2:5 N aqueous NaOH (4 mL) and Triton B (1 mL) followed by 2-(4'-bromomethylbiphenyl)-t-butylsulfonamide [prepared according to the procedure described in U.S. Pat. No. 5,126,342] (4.2 g, 11 mMol). The mixture was stirred at 85° C. for 12 h and then cooled to room temperature. The reaction was diluted with ethylacetate (100 mL), and the organic phase was washed with water (3×50 mL), and then dried over MgSO4. The ethylacetate layer was filtered and concentrated in vacuo to a small volume (~10 mL). Dry ether (100 mL) was added and the precipitate formed was filtered and dried. The crude product was then recrystallized from hot ethylacetate to give the desired product 4-p-toluyl-2-(2'-t-butylaminosulfonyl)-biphen-4-yl)methyl-phthalazin-1-(2H)-one as white crystalline solid (4.3 g).

1. additionwere added 2
2. customprepared
3. temperaturecooled to room temperature
4. washthe organic phase was washed with water (3×50 mL)
5. dry with materialdried over MgSO4
6. filtrationThe ethylacetate layer was filtered
7. concentrationconcentrated in vacuo to a small volume (~10 mL)
8. additionDry ether (100 mL) was added
9. customthe precipitate formed
10. filtrationwas filtered
11. customdried
12. customThe crude product was then recrystallized from hot ethylacetate

ORD record

ord-72be7109f5bb4b3ea49c975993e78e96

Source dataset

uspto-grants-1997_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05668279