Acetic Acid → {4-[4-[(Difluoromethyl)oxy]-9-(ethyloxy)-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-3-fluorophenyl}acetic acid

HRID 222438Notes

Reaction equation

HRID 222438 reaction equation
[F:1][CH:2]([F:34])[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.C(O)(=O)C.Cl>O>[F:34][CH:2]([F: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

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 58231465Ethyl {4-[4-[(difluoromethyl)oxy]-9-(ethyloxy)-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-3-fluorophenyl}acetate

Product 1

HCID 24738722{4-[4-[(Difluoromethyl)oxy]-9-(ethyloxy)-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-3-fluorophenyl}acetic acidYield 85.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl {-4-[4-[(difluoromethyl)oxy]-9-(ethyloxy)-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-3-fluorophenyl}acetate (0.60 g, 1.27 mmol) was heated to 100° C. in a 1:1 mixture of acetic acid:2N aqueous hydrochloric acid (20 ml) for 50 minutes. The reaction was cooled to room temperature. On addition of water, the resulting white solid was collected by filtration, washed with water and dried under vacuum to give the title compound (0.516 g, 1.09 mmol).

Workup

  1. filtrationthe resulting white solid was collected by filtration
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-caf7dd5ad56545738015dcfcf4de9056
Source dataset
uspto-grants-2012_06
Patent number
US08207213B2

Reaction notes

Loading…