7-Methylisatin → 2-(4-chlorobenzyl)-3-hydroxy-8-methylquinoline-4-carboxylic Acid

HRID 2375516Notes

Reaction equation

HRID 2375516 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]4C=CC=CC=4)[CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[CH:4][CH:3]=1.CC1C=CC=C2C=1NC(=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](=[C:10]([CH3:21])[CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 143137-MethylisatinHCID 113837082-(4-Chloro-benzyl)-3-hydroxy-8-phenyl-quinoline-4-carboxylic AcidHCID 122224641-(Acetyloxy)-3-(4-chlorophenyl)-2-propanone

Product 1

HCID 117389342-(4-chlorobenzyl)-3-hydroxy-8-methylquinoline-4-carboxylic AcidYield 38%

Procedure

This compound was synthesized by the procedure described above for Compound 2, reacting 7-methyl-1H-indole-2,3-dione (1.00 g, 6.21 mmol) with intermediate 2 (1.76 g, 7.76 mmol). The crude acid was purified as described above for Compound 3 to give Compound 6 as a bright yellow powder (0.774 g, 38% yield): 1H NMR (400 MHz, DMSO-D6) δ 2.65 (s, 3H) 4.33 (s, 2H) 7.35 (m, 4H) 7.44 (m, 2H) 8.30 (dd, J=8.1, 1.3 Hz, 1H).

Workup

  1. customThis compound was synthesized by the procedure
  2. customThe crude acid was purified

Sources & evidence

ORD record
ord-da120a1634784c2bbc3f34e99c16fa1e
Source dataset
uspto-grants-2008_12
Patent number
US07465799B2

Reaction notes

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