Calcium acetate monohydrate → n-Ethyl-n-phenyl-5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide calcium salt

HRID 733433Notes

Reaction equation

HRID 733433 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].O.C([O-])(=O)C.[Ca+2:32].C([O-])(=O)C>C(O)C.O>[Ca:32].[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

5

Reactant 2

HCID 82163Calcium acetate monohydrateHCID 66586725Laquinimod (sodium)

Product 1

HCID 67081989n-Ethyl-n-phenyl-5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide calcium saltYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

N-Ethyl-N-phenyl- 5chloro- 1,2-dihydro- 4-hydroxy- 1-methyl- 2-oxo- 3-quinolinecarboxamide sodium salt ( 2.63 mmol, 1.0 g) was dissolved in a mixture of ethanol ( 10.5 ml) and water ( 5.3 ml). The solution was heated to 70° C. and a solution of calcium acetate hydrate in water ( 1M solution, 1.05 eq., 1.38 mmol, 1.38 ml) was added. The resulting suspension was stirred for 30 minutes, then cooled, and the crystals were isolated by filtration, washed with water, and dried under vacuum ( 966 mg, 98% yield). Anal. Calcd for C38H32Cl2N4O6Ca: C, 60.7; H, 4.29; N, 7.45. Found C, 60.5; H, 4.34; N, 7.41.

Workup

  1. temperaturecooled
  2. customthe crystals were isolated by filtration
  3. washwashed with water
  4. customdried under vacuum ( 966 mg, 98% yield)

Sources & evidence

ORD record
ord-6413c7360b20444b8a2510fd4f2c6b6d
Source dataset
uspto-grants-2009_09
Patent number
US07589208B2

Reaction notes

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