Chloroform → N-Ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide zinc salt

HRID 406304Notes

Reaction equation

HRID 406304 reaction equation
[CH2:1]([N:3]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:4]([C:6]1[C:7](=[O:20])[N:8]([CH3:19])[C:9]2[C:14]([C:15]=1[OH:16])=[C:13]([CH2:17][CH3:18])[CH:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2].[OH-].[Na+].C(Cl)(Cl)Cl.O.O.C([O-])(=O)C.[Zn+2:39].C([O-])(=O)C>C(O)C.O>[Zn:39].[CH2:1]([N:3]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:4]([C:6]1[C:7](=[O:20])[N:8]([CH3:19])[C:9]2[C:14]([C:15]=1[OH:16])=[C:13]([CH2:17][CH3:18])[CH:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 2724192Zinc acetate (USP)HCID 54684617Paquinimod

Product 1

HCID 67082049N-Ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide zinc saltYield 76%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-Ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide (1.0 g, 2.85 mmol) was dissolved in a mixture of 1M NaOH (2.95 mmol, 2.95 ml) and ethanol (6.0 ml). Chloroform (20 ml) and water (40 ml) were added followed by addition of zinc acetate dihydrate (3.0 mmol, 660 mg). The two-phase mixture was stirred vigorously for 10 min, the organic phase was separated and dried with sodium sulphate and the solvents were removed. The residue was recrystallised from methanol to give the title compound (823 mg, 76% yield). Anal. Calcd for C42H42N4O6Zn: C, 66.01; H, 5.54; N, 7.33. Found C, 65.4; H, 5.68; N, 7.29. EDTA-titriometric determination of zinc gave a content of 8.45% (theoretical content is 8.50%), The solubility in water at room temperature was 0.3 mg/ml.

Workup

  1. customthe organic phase was separated
  2. dry with materialdried with sodium sulphate
  3. customthe solvents were removed
  4. customThe residue was recrystallised from methanol

Sources & evidence

ORD record
ord-2e76a9c9c1f34504ad534d1b8153a810
Source dataset
uspto-grants-2014_06
Patent number
US08754104B2

Reaction notes

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