Sodium Hydroxide → {3-Chloro-4-[4-[(difluoromethyl)oxy]-9-(ethyloxy)-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]phenyl}acetic acid

HRID 222435Notes

Reaction equation

HRID 222435 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:29][C:30]([O:32]CC)=[O:31])[CH:5]=[CH:6][C:7]=1[N:8]1[C:16](=[O:17])[C:15]2[C:14]([O:18][CH2:19][CH3:20])=[C:13]3[CH:21]=[CH:22][CH:23]=[CH:24][C:12]3=[C:11]([O:25][CH:26]([F:28])[F:27])[C:10]=2[CH2:9]1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:29][C:30]([OH:32])=[O:31])[CH:5]=[CH:6][C:7]=1[N:8]1[C:16](=[O:17])[C:15]2[C:14]([O:18][CH2:19][CH3:20])=[C:13]3[CH:21]=[CH:22][CH:23]=[CH:24][C:12]3=[C:11]([O:25][CH:26]([F:28])[F:27])[C:10]=2[CH2:9]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58231518HCID 58231518, compound

Product 1

HCID 24738562{3-Chloro-4-[4-[(difluoromethyl)oxy]-9-(ethyloxy)-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]phenyl}acetic acidYield 94.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl {3-chloro-4-[4-[(difluoromethyl)oxy]-9-(ethyloxy)-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]phenyl}acetate (0.141 g, 0.288 mmol) was heated to reflux in a 1:1 mixture of 2N sodium hydroxide:ethanol (6 ml) for 1.5 hours. The reaction was cooled to room temperature. The ethanol was evaporated and the mixture acidified with 2N aqueous hydrochloric acid. The resulting white solid was collected by filtration, washed with water and dried under vacuum to give the title compound (0.125 g, 0.271 mmol). LC/MS: Rt=3.19, [MH]+ 462.

Workup

  1. customThe ethanol was evaporated
  2. filtrationThe resulting white solid was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-bd8bb716570a48c09148254dda56c30c
Source dataset
uspto-grants-2012_06
Patent number
US08207213B2

Reaction notes

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