7-Bromoisatin → 8-bromo-2-(4-chlorobenzyl)-3-hydroxyquinoline-4-carboxylic Acid

HRID 2375519Notes

Reaction equation

HRID 2375519 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.[Br:29]C1C=CC=C2C=1NC(=O)C2=O.C(OCC(=O)CC1C=CC(Cl)=CC=1)(=O)C>>[Br:29][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[C:7]([CH2:6][C:5]1[CH:27]=[CH:28][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:16]([OH:17])=[C:15]2[C:18]([OH:20])=[O:19]

Participants

4

Reactant 3

HCID 23023537-BromoisatinHCID 113837082-(4-Chloro-benzyl)-3-hydroxy-8-phenyl-quinoline-4-carboxylic AcidHCID 122224641-(Acetyloxy)-3-(4-chlorophenyl)-2-propanone

Product 1

HCID 114861898-bromo-2-(4-chlorobenzyl)-3-hydroxyquinoline-4-carboxylic AcidYield 23%

Procedure

This compound was synthesized by the procedure described above for Compound 2, reacting 7-Bromo-1H-indole-2,3-dione (1.00 g, 4.42 mmol) with intermediate 2 (1.25 g, 5.53 mmol). The crude acid was purified as described above for Compound 3, then recrystallized from acetonitrile to give product as large, bright yellow crystals (Compound 9, 0.398 g, 23% yield): 1H NMR (400 MHz, DMSO-D6) δ 4.35 (s, 2H) 7.35 (m, 4H) 7.46 (dd, J=8.6, 7.6 Hz, 1H) 7.92 (dd, J=7.5, 1.1 Hz, 1H) 8.50 (dd, J=8.6, 1.3 Hz, 1H); HRMS (ESI/FTMS) calcd for C17H12BrClNO3 (MH+) 391.9684, found 391.9689. Anal. Calcd for C17H11BrClNO3: C, 52.00; H, 2.82; N, 3.57. Found: C, 51.72; H, 2.77; N, 3.53.

Workup

  1. customThis compound was synthesized by the procedure
  2. customThe crude acid was purified
  3. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-f5be9eb5c3b3413e88bacf485ead5b1a
Source dataset
uspto-grants-2008_12
Patent number
US07465799B2

Reaction notes

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