Chloroform → N-Ethyl-N-phenyl-5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide iron (III) salt

HRID 406302Notes

Reaction equation

HRID 406302 reaction equation
[Na].[CH2:2]([N:4]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:5]([C:7]1[C:8](=[O:20])[N:9]([CH3:19])[C:10]2[C:15]([C:16]=1[OH:17])=[C:14]([Cl:18])[CH:13]=[CH:12][CH:11]=2)=[O:6])[CH3:3].C(Cl)(Cl)Cl.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+3:41].S([O-])([O-])(=O)=O.S([O-])([O-])(=O)=O.[Fe+3].[OH-].[Na+]>O>[Fe+3:41].[CH2:2]([N:4]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:5]([C:7]1[C:8](=[O:20])[N:9]([CH3:19])[C:10]2[C:15]([C:16]=1[OH:17])=[C:14]([Cl:18])[CH:13]=[CH:12][CH:11]=2)=[O:6])[CH3:3]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 23443659Sulfuric acid, iron(3+) salt (3:2), pentahydrateHCID 66586725Laquinimod (sodium)

Product 1

HCID 86600440N-Ethyl-N-phenyl-5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide iron (III) saltYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

N-Ethyl-N-phenyl-5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide sodium salt (5.0 g, 13.2 mmol) was dissolved in water (80 ml) at 40° C. and chloroform (100 ml) was added. A solution of iron(III)sulphate pentahydrate (0.95 eq., 2.09 mmol, 1.023 g) dissolved in water (30 ml) was added. The two-phase system was stirred vigorously and pH in the aqueous phase was adjusted to 8 with 1 M NaOH. The deep-red organic phase was separated, dried with sodium sulphate, and solvents were removed to give the title compound as a red amorphous glassy mass (4.22 g, 85% yield). MS-ESI: m/z 1122 [MH]+. The glassy mass was dissolved in methanol and red crystals of the title compound were formed. The crystals were filtered, washed with methanol, and dried under vacuum to give the title compound (3.96 g, 80% yield). Anal. Calcd for C57H48N6O9Cl3Fe: C, 61.0; H, 4.31; N, 7.48, Found C, 62.7; H, 4.37; N, 7.27, EDTA-titriometric determination of iron (III) gave a content of 4.90% (theoretical content is 4.97%).

Workup

  1. additionwas added
  2. customThe deep-red organic phase was separated
  3. dry with materialdried with sodium sulphate, and solvents
  4. customwere removed

Sources & evidence

ORD record
ord-a699ac39933247928c9c011303a3b45a
Source dataset
uspto-grants-2014_06
Patent number
US08754104B2

Reaction notes

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