Acetonitrile → HCID 69080459, compound

HRID 1782041Notes

Reaction equation

HRID 1782041 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([NH:14][C:15]3C=[CH:19][C:18](OC)=[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+].C(#[N:34])C>O1CCOCC1.O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([NH:14][C:15]3[C:16]([CH3:23])=[CH:17][CH:18]=[CH:19][N:34]=3)=[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

6

Reactant 3

HCID 6342Acetonitrile2×HCID 14798Sodium HydroxideHCID 69079973HCID 69079973, compound

Product 1

HCID 69080459HCID 69080459, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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. The pure product was isolated from the reaction solution by chromatography on an HPLC system. 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. customThe pure product was isolated from the reaction solution by chromatography on an HPLC system
  4. customrose to 95% over the course of 20 minutes

Sources & evidence

ORD record
ord-3c28c741a2714e57b6727b2b6fba0cab
Source dataset
uspto-grants-2009_03
Patent number
US07498341B2

Reaction notes

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