Citric Acid → Flunixin

HRID 1888132Notes

Reaction equation

C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[CH3:14][C:15]1[C:20]([NH:21][C:22]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([OH:30])=[O:29])=[CH:19][CH:18]=[CH:17][C:16]=1[C:31]([F:34])([F:33])[F:32].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>[CH3:14][C:15]1[C:20]([NH:21][C:22]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([OH:30])=[O:29])=[CH:19][CH:18]=[CH:17][C:16]=1[C:31]([F:33])([F:32])[F:34]

Participants

Reactant 2

HCID 311Citric Acid

HCID 39212Flunixin Meglumine

Product 1

HCID 38081FlunixinYield 94%

Procedure

50% Aqueous citric acid solution is added to about 0.5 L of Banamine Solution while maintaining the temperature at less than 30° C. The resulting mixture was agitated for about 1 hour while continuing to maintain the temperature at less than 30° C. The precipitated Flunixin was collected by filtration and washed with 0.5 L of water, then dried at about 50-60° C. to a moisture content of less than 1% to yield about 23.5 g of crude Flunixin (94%)

Workup

temperaturewhile maintaining the temperature at less than 30° C
temperatureto maintain the temperature at less than 30° C
filtrationThe precipitated Flunixin was collected by filtration
washwashed with 0.5 L of water
customdried at about 50-60° C. to a moisture content of less than 1%

Sources & evidence

ORD record: ord-af5a3994cf41404192c87068a8c07cdb
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501788B2

Reaction notes

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