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

HRID 1878644Notes

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+].O.C([O-])(=O)C.[Ca+2:34].C([O-])(=O)C>C(O)C.O>[Ca:34].[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

Conditions

Temperature: 70 °C

Procedure

N-Ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide (5.0 g, 14.2 mmol) was dissolved in a mixture of 1M NaOH (14.26 mmol, 14.26 ml) and ethanol (30 ml), and pH was adjusted to 7.5. The solution was heated to 70° C. and calcium acetate hydrate (1.05 eq., 7.5 mmol, 1.335 g) in water (7 ml) was added dropwise during 5 min. The heating was discontinued and the mixture was stirred at room temperature for 1 h, the crystals were filtered, washed with ethanol/water 1/1, and dried under vacuum to afford the title compound (5.16 g, 98% yield). Anal. Calcd for C42H42N4O6Ca: C, 68.3; H, 5.73; N, 7.58. Found C, 68.4; H, 5.72; N, 7.63. EDTA-titriometric determination of calcium gave a content of 5.42% (theoretical content is 5.42%).

Workup

filtrationthe crystals were filtered
washwashed with ethanol/water 1/1
customdried under vacuum

Sources & evidence

ORD record: ord-dc7cb1ae01cf4203a046ad8784f23a61
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314124B2

Reaction notes

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