Sodium Hydroxide → HCID 69309236, compound

HRID 749483Notes

Reaction equation

HRID 749483 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=3[CH3:23])=[CH:10][C:11]=2[CH3:13])[C:6](=[O:24])[CH:5]([C:25]([O:27]C)=[O:26])[C:4]1=[O:29])[CH3:2].[OH-].[Na+]>O1CCOCC1>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=3[CH3:23])=[CH:10][C:11]=2[CH3:13])[C:6](=[O:24])[CH:5]([C:25]([OH:27])=[O:26])[C:4]1=[O:29])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69079973HCID 69079973, compound

Product 1

HCID 69309236HCID 69309236, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 1-ethyl-6-(4-methoxy-2-methylphenylamino)-8-methyl-4-oxo-1,4-dihydroquinolone-3-carboxylate (30 mg) was dissolved in 5 ml of dioxane, 2.5 equivalents of a 1 N NaOH solution were added, and the mixture was heated at 60° C. for 4 h. Removal of the solvent in vacuo was followed by chromatography on an HPLC system to purify the product. This entailed use of a Merck Purospher-RP18 column and an acetonitrile:water mixture as eluent; the initial acetonitrile content was 15% and rose to 95% over the course of 20 minutes.

Workup

  1. customRemoval of the solvent in vacuo
  2. customto purify the product
  3. customrose to 95% over the course of 20 minutes

Sources & evidence

ORD record
ord-5bd10326404f42fd8d7a64f701384f9c
Source dataset
uspto-grants-2008_07
Patent number
US07402674B2

Reaction notes

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