Sodium Hydroxide → HCID 24739203, compound

HRID 889492Notes

Reaction equation

HRID 889492 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])=[CH:15][C:14]=3[F:25])[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])=[CH:15][C:14]=3[F:25])[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 58399561HCID 58399561, compound

Product 1

HCID 24739203HCID 24739203, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl {4-[4,9-bis(ethyloxy)-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-3-fluorophenyl}acetate (0.072 g, 0.16 mmol) was suspended in ethanol (2 ml) and treated with 2N sodium hydroxide (6 ml). Heated to reflux at 100° C. under argon for 1 hour. The reaction was shown to be complete by LC/MS. The reaction mixture was cooled and the solvent evaporated to dryness. Water and 2N HCl was added to acidify. This was extracted with ethyl acetate (×2), dried over magnesium sulphate and evaporated to a solid which was dried overnight in a vacuum oven to give the title compound (0.038 g, 0.09 mmol).

Workup

  1. temperatureHeated
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent evaporated to dryness
  4. additionWater and 2N HCl was added
  5. extractionThis was extracted with ethyl acetate (×2)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated to a solid which
  8. customwas dried overnight in a vacuum oven

Sources & evidence

ORD record
ord-6c98abda82a6430ebd25ce03d077d3de
Source dataset
uspto-grants-2012_08
Patent number
US08252833B2

Reaction notes

Loading…