Sulfuric Acid → 5,7-Difluoro-1,2-dihydroquinolin-2-one

HRID 656935Notes

Reaction equation

OS(O)(=O)=O.[F:6][C:7]1[CH:8]=[C:9]([NH:14][C:15](=[O:22])[CH2:16][CH:17](OC)OC)[CH:10]=[C:11]([F:13])[CH:12]=1>O>[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]2[C:8]=1[CH:17]=[CH:16][C:15](=[O:22])[NH:14]2

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of 70% H2SO4 was made up by adding chilled H2SO4 (70 ml) to chilled water (30 ml) ensuring the temp remained between 10-20° C. The acid was then slowly added to the water keeping the temperature between 10 and 20° C. Finely ground N-(3,5-difluorophenyl)-3,3-bis(methyloxy)propanamide (12 g, 49 mmol) was added to the chilled solution over 1 h and then stirred at 5° C. for 1.5 h. An ice-water mixture (100 ml) was added carefully, followed by water (400 ml). The mixture was stirred for 0.5 h then the solid formed was filtered off and dried in the vacuum-oven at 40° C. over the weekend. The solid was still wet so it was dried in the desiccator with P2O5 to afford the impure desired compound (12 g, 136%).

Workup

additionby adding
customremained between 10-20° C
stirringThe mixture was stirred for 0.5 h
customthe solid formed
filtrationwas filtered off
customdried in the vacuum-oven at 40° C. over the weekend
dry with materialwas dried in the desiccator with P2O5

Sources & evidence

ORD record: ord-97981a5284e04f05bd1b8dcec62dcd66
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071592B2

Reaction notes

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