Acetic Acid → (4-(4,9-bis(ethyloxy)-1-oxo-1,3-dihydro-2H-benzo(f)isoindol-2-yl)-2-fluorophenyl)acetic acid

HRID 889503Notes

Reaction equation

[CH2:1]([O:3][C:4]1[C:12]2[CH2:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]CC)=[O:21])=[C:15]([F:25])[CH:14]=3)[C:9](=[O:26])[C:8]=2[C:7]([O:27][CH2:28][CH3:29])=[C:6]2[CH:30]=[CH:31][CH:32]=[CH:33][C:5]=12)[CH3:2].C(O)(=O)C.Cl.ClCCl>CO>[CH2:1]([O:3][C:4]1[C:12]2[CH2:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[C:15]([F:25])[CH:14]=3)[C:9](=[O:26])[C:8]=2[C:7]([O:27][CH2:28][CH3:29])=[C:6]2[CH:30]=[CH:31][CH:32]=[CH:33][C:5]=12)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of ethyl {-4-[4,9-bis(ethyloxy)-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-2-fluorophenyl}acetate (200.0 g, 443 mmol) in a mixture of glacial acetic acid (2080 mL) and hydrochloric acid (2 M, 700 mL) was heated to reflux under a nitrogen atmosphere, with the reaction progress monitored by TLC analysis (silica, dichloromethane:methanol, 99:1). After 60 minutes the reaction mixture was cooled to 0° C. The precipitated solid was isolated by filtration, washed with water (1400 mL), and freeze-dried to give the desired product as an off-white solid (163.4 g, 87% yield).

Workup

temperaturewas heated
temperatureto reflux under a nitrogen atmosphere, with the reaction progress
customThe precipitated solid was isolated by filtration
washwashed with water (1400 mL)
customfreeze-dried

Sources & evidence

ORD record: ord-a8464b11ca354405a7e7aecb64698890
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252833B2

Reaction notes

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