Hydrochloric Acid → N-Ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide calcium salt

HRID 406303Notes

Reaction equation

HRID 406303 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+].Cl.O.C([O-])(=O)C.[Ca+2:35].C([O-])(=O)C>O>[Ca:35].[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 82163Calcium acetate monohydrateHCID 54684617Paquinimod

Product 1

HCID 67082083N-Ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide calcium saltYield 153%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

N-ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide (28.5 mmol, 10.0 g) was dissolved in a mixture of water (200 mL) and 10M NaOH (28.5 mmol, 2.85 mL), and pH was adjusted to 7.5-8.0 with 1M HCl. To this solution at 50° C. was added during 15 min a solution of calcium acetate hydrate (15 mmol, 2.67 g) in water (50 ml) and the resultant thick emulsion was allowed to cool to room temperature and the precipitate was filtered and washed with water. The precipitate was dried in vacuum to give 8.96 g of an amorphous calcium salt.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with water
  3. customThe precipitate was dried in vacuum

Sources & evidence

ORD record
ord-13aee7b1eedd4994a1944220c2c82633
Source dataset
uspto-grants-2014_06
Patent number
US08754104B2

Reaction notes

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