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

HRID 913182Notes

Reaction equation

HRID 913182 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:32][C:33]([O:35]CC)=[O:34])[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][CH3:30])[C:10]=2[C:9]1=[O:31].C(O)(=O)C.Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:32][C:33]([OH:35])=[O:34])[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:21])[F:22])=[C:13]3[CH:24]=[CH:25][CH:26]=[CH:27][C:12]3=[C:11]([O:28][CH2:29][CH3:30])[C:10]=2[C:9]1=[O:31]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 58012482Ethyl (3-chloro-4-{4-(ethyloxy)-1,3-dioxo-9-[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate

Product 1

HCID 24760118(3-Chloro-4-{4-(ethyloxy)-1,3-dioxo-9-[(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-{4-(ethyloxy)-1,3-dioxo-9-[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate (0.060 g, 0.11 mmol) was heated to 100° C. in a 1:1 mixture of acetic acid:HCl (2N) (6 ml) for 1.25 hours. On addition of water, the resulting white solid was collected by filtration and washed with water (0.047 g, 0.09 mmol). LC/MS: Rt=3.44, [MH]+ 508.

Workup

  1. filtrationthe resulting white solid was collected by filtration

Sources & evidence

ORD record
ord-267d9950df2c4b7c80b74ec4dca561b8
Source dataset
uspto-grants-2011_09
Patent number
US08026270B2

Reaction notes

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