5-(trifluoromethoxy)-2,3-dihydro-1H-indole-2,3-dione → HCID 59855099, compound

HRID 2375523Notes

Reaction equation

HRID 2375523 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][C:7]2[C:16]([OH:17])=[C:15]([C:18]([OH:20])=[O:19])[C:14]3[C:9](=[C:10](C4C=CC=CC=4)[CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[CH:4][CH:3]=1.[F:29][C:30]([F:44])([F:43])[O:31]C1C=C2C(=CC=1)NC(=O)C2=O.C(OCC(=O)CC1C=CC(Cl)=CC=1)(=O)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:16]([OH:17])=[C:15]([C:18]([OH:20])=[O:19])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:31][C:30]([F:44])([F:43])[F:29])[CH:13]=3)[N:8]=2)=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 27327525-(trifluoromethoxy)-2,3-dihydro-1H-indole-2,3-dioneHCID 113837082-(4-Chloro-benzyl)-3-hydroxy-8-phenyl-quinoline-4-carboxylic AcidHCID 122224641-(Acetyloxy)-3-(4-chlorophenyl)-2-propanone2×

Product 1

HCID 59855099HCID 59855099, compoundYield 50%

Procedure

This compound was synthesized according to the procedure described above for Compound 2, reacting 5-trifluoromethoxyisatin (1.4 g, 6.06 mmol) with 3-(4-chlorophenyl)-2-oxopropyl acetate, Intermediate 2 (1.72 g, 7.57 mmol). The crude acid was recrystallized from ethanol to give pure product as a yellow powder Compound 14 (1.2 g, 50% yield): 1H NMR (400 MHz, DMSO-D6) δ ppm 4.32 (s, 2H) 7.26-7.40 (m, 4H) 7.47 (d, J=9.09 Hz, 1H) 8.00 (d, J=8.84 Hz, 1H) 8.86 (s, 1H).

Workup

  1. customThis compound was synthesized
  2. customThe crude acid was recrystallized from ethanol

Sources & evidence

ORD record
ord-94d05289e5914b0cabf5769b62655fa8
Source dataset
uspto-grants-2008_12
Patent number
US07465799B2

Reaction notes

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