2-(4-Chloro-benzyl)-3-hydroxy-8-phenyl-quinoline-4-carboxylic Acid → 2-(4-chlorobenzyl)-8-(fur-3-yl)-3-hydroxyquinoline-4-carboxylic Acid

HRID 2375521Notes

Reaction equation

HRID 2375521 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]([C:21]4[CH:26]=CC=[CH:23][CH:22]=4)[CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[CH:4][CH:3]=1.[O:29]1C=CC(C2C=CC=C3C=2NC(=O)C3=O)=C1.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](=[C:10]([C:21]4[CH:22]=[CH:23][O:29][CH:26]=4)[CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 113837082-(4-Chloro-benzyl)-3-hydroxy-8-phenyl-quinoline-4-carboxylic AcidHCID 122224641-(Acetyloxy)-3-(4-chlorophenyl)-2-propanone2×HCID 161001987-(Furan-3-yl)-1H-indole-2,3-dione2×

Product 1

HCID 111881552-(4-chlorobenzyl)-8-(fur-3-yl)-3-hydroxyquinoline-4-carboxylic AcidYield 15%

Procedure

This compound was synthesized according to the procedure described above for Compound 2, reacting 7-(fur-3-yl)isatin, Intermediate 10 (0.84 g, 3.9 mmol) with 3-(4-chlorophenyl)-2-oxopropyl acetate, Intermediate 2 (1.11 g, 4.91 mmol). The crude acid was purified as described above for Compound 3 to give pure product, a mustard-yellow powder Compound 12 (0.217 g, 15% yield): 1H NMR (400 MHz, DMSO-D6) δ 4.40 (s, 2H) 7.09 (d, J=1.8Hz, 1H) 7.39 (q, J=8.6 Hz, 4H) 7.56 (dd, J=8.46, 7.5 Hz, 1H) 7.67 (t, J=1.8 Hz, 1H) 7.84 (dd, J=7.3, 1.3 Hz, 1H) 8.07 (s, 1H) 8.30 (dd, J=8.6, 1.0 Hz, 1H).

Workup

  1. customThis compound was synthesized
  2. customThe crude acid was purified
  3. customto give pure product

Sources & evidence

ORD record
ord-f02e162aa5274aa68fa800b14830406a
Source dataset
uspto-grants-2008_12
Patent number
US07465799B2

Reaction notes

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