Acetic Acid → (3-Chloro-4-{1,3-dioxo-4,9-bis[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetic acid

HRID 913168Notes

Reaction equation

HRID 913168 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:35][C:36]([O:38]CC)=[O:37])[CH:5]=[CH:6][C:7]=1[N:8]1[C:16](=[O:17])[C:15]2[C:14]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[C:13]3[CH:24]=[CH:25][CH:26]=[CH:27][C:12]3=[C:11]([O:28][CH2:29][C:30]([F:33])([F:32])[F:31])[C:10]=2[C:9]1=[O:34].C(O)(=O)C.Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:35][C:36]([OH:38])=[O:37])[CH:5]=[CH:6][C:7]=1[N:8]1[C:16](=[O:17])[C:15]2[C:14]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[C:13]3[CH:24]=[CH:25][CH:26]=[CH:27][C:12]3=[C:11]([O:28][CH2:29][C:30]([F:32])([F:33])[F:31])[C:10]=2[C:9]1=[O:34]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 58012483Ethyl (3-chloro-4-{1,3-dioxo-4,9-bis[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate

Product 1

HCID 24760115(3-Chloro-4-{1,3-dioxo-4,9-bis[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Ethyl (3-chloro-4-{1,3-dioxo-4,9-bis[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate (0.375 g, 0.64 mmol) was heated to 100° C. in a 1:1 mixture of acetic acid:2N aqueous hydrochloric acid (20 ml) for 5 hours. The reaction was cooled to room temperature. On addition of water, the resulting white solid was collected by filtration and washed with water (0.315 g, 0.56 mmol). LC/MS: Rt=3.57, [MH]+ 562.

Workup

  1. filtrationthe resulting white solid was collected by filtration

Sources & evidence

ORD record
ord-fc70a381ec154322a1e5d18f23f1bdb3
Source dataset
uspto-grants-2011_09
Patent number
US08026270B2

Reaction notes

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