7-Fluoroisatin → 2-(4-chlorobenzyl)-8-fluoro-3-hydroxyquinoline-4-carboxylic Acid

HRID 2375522Notes

Reaction equation

HRID 2375522 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]C1C=CC=C2C=1NC(=O)C2=O.C(OCC(=O)CC1C=CC(Cl)=CC=1)(=O)C>>[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]([F:29])[CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 5864187-FluoroisatinHCID 113837082-(4-Chloro-benzyl)-3-hydroxy-8-phenyl-quinoline-4-carboxylic AcidHCID 122224641-(Acetyloxy)-3-(4-chlorophenyl)-2-propanone2×

Product 1

HCID 114275322-(4-chlorobenzyl)-8-fluoro-3-hydroxyquinoline-4-carboxylic AcidYield 10%

Procedure

This compound was synthesized according to the procedure described above for Compound 2, reacting 7-fluoroisatin (1.00 g, 6.06 mmol) with 3-(4-chlorophenyl)-2-oxopropyl acetate, Intermediate 2 (1.72 g, 7.57 mmol). The crude acid was purified as described above for Compound 3, then recrystallized from ethanol/benzene to give pure product as an off-white powder Compound 13 (0.206 g, 10% yield): 1H NMR (400 MHz, DMSO-D6) δ 4.34 (s, 2H) 7.37 (m, 5H) 7.55 (m, 1H) 8.34 (d, J=8.6 Hz, 1H).

Workup

  1. customThis compound was synthesized
  2. customThe crude acid was purified
  3. customrecrystallized from ethanol/benzene

Sources & evidence

ORD record
ord-f6172b2652444368b66fe55813172c4f
Source dataset
uspto-grants-2008_12
Patent number
US07465799B2

Reaction notes

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