1,4-Dioxane → HCID 135503627, compound

HRID 1455505Notes

Reaction equation

HRID 1455505 reaction equation
C1(N[C:8]([C:10]2[C:11]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[C:15]([OH:20])[CH:14]=3)=[O:9])C=CC=CC=1.[O:29]1CCOCC1>Cl>[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:21][C:11]1[C:10]([C:8]([OH:29])=[O:9])=[CH:19][C:18]2[C:13](=[CH:14][C:15]([OH:20])=[CH:16][CH:17]=2)[N:12]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 135525315HCID 135525315, compound

Product 1

HCID 135503627HCID 135503627, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 2-(2-Chloro-phenylamino)-7-hydroxy-quinoline-3-carboxylic acid phenylamide (17 mg, 0.04 mmol) in 16N aqueous HCl (0.1 ml) and 1,4-Dioxane (0.1 ml) was heated at reflux for 5 days. After evaporating the solvent, the residue was recrystallized from methanol to give 2-(2-Chloro-phenylamino)-7-hydroxy-quinoline-3-carboxylic acid as the white crystal; 13 mg (99%). 1H NMR (400 MHz, DMSO-d6) ppm 6.96 (dd, 1H, J=2.3, 8.6 Hz), 6.99 (d, 1H. J=2.3 Hz), 7.04 (ddd, 1H, J=1.5, 7.8, 8.8 Hz), 7.40 (ddd, 1H, J=1.5, 7.8, 8.8 Hz), 7.52 (dd, 1H, J=1.5, 7.8 Hz), 7.83 (d, 1H, J=8.8 Hz), 8.84 (s, 1H), 9.10 (d, 1H, J=11.2 Hz), 10.48 (s, 1H), 11.05 (s, 1H). LC/MS: m/z 315 (M+1)+, 313 (M−1)−.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 days
  3. customAfter evaporating the solvent
  4. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-19dfb718d60c46aa93cd3ebf9bb50fbf
Source dataset
uspto-grants-2009_01
Patent number
US07482455B2

Reaction notes

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