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

HRID 889493Notes

Reaction equation

HRID 889493 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].[OH-].[Na+]>C(O)C>[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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58399571Ethyl {4-[4,9-bis(ethyloxy)-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-2-fluorophenyl}acetate

Product 1

HCID 16678098(4-(4,9-bis(ethyloxy)-1-oxo-1,3-dihydro-2H-benzo(f)isoindol-2-yl)-2-fluorophenyl)acetic acidYield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl {4-[4,9-bis(ethyloxy)-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-2-fluorophenyl}acetate (20.2 g, 44.8 mmol) was suspended in ethanol (450 ml) and treated with 2N sodium hydroxide (150 ml). The mixture was heated under reflux for 1 hour then cooled, and concentrated in vacuo to ˜200 ml, then acidified with 2N hydrochloric acid. The white solid was collected by filtration, washed with water (500 ml) and dried in a vacuum oven to yield the title compound as a cream solid (18.45 g, 43.6 mmol).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperaturethen cooled
  4. concentrationconcentrated in vacuo to ˜200 ml
  5. filtrationThe white solid was collected by filtration
  6. washwashed with water (500 ml)
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-0f2c0d1a2d904a11acc6a69db4cd09ca
Source dataset
uspto-grants-2012_08
Patent number
US08252833B2

Reaction notes

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