Niflumic Acid → Talniflumate

HRID 1863208Notes

Reaction equation

HRID 1863208 reaction equation
C(N(CC)CC)C.Br[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11](=[O:12])[O:10]1.[F:19][C:20]([F:38])([F:37])[C:21]1[CH:22]=[C:23]([CH:34]=[CH:35][CH:36]=1)[NH:24][C:25]1[N:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([OH:29])=[O:28]>O>[F:38][C:20]([F:19])([F:37])[C:21]1[CH:22]=[C:23]([CH:34]=[CH:35][CH:36]=1)[NH:24][C:25]1[C:26]([C:27]([O:29][CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:11](=[O:12])[O:10]2)=[O:28])=[CH:30][CH:31]=[CH:32][N:33]=1

Participants

5

Reactant 3

HCID 4488Niflumic AcidHCID 8471TriethylamineHCID 962181(3H)-Isobenzofuranone, 3-bromo-

Product 1

HCID 48229TalniflumateYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Triethylamine (20 ml) and 3-bromophthalide (21.3 g) were added to a suspension of 2(3'-trifluormethylanilino)-nicotinic acid (28,2 g in 500 ml of acetone). The mixture was refluxed during 4 hours. The obtained greenish yellow suspension was poured into 6000 ml of water, which was previously heated at 50° C. The stirred reaction mixture was cooled to 5° C., and the formed precipitate was filtered and washed with cool water. Yield: 52% (20.5 g) of phthalidyl 2-(3'-trifluormethylanilino)-pyridin-3-carboxylate, m.p: 162°-164° C.

Workup

  1. temperatureThe mixture was refluxed during 4 hours
  2. customThe stirred reaction mixture
  3. temperaturewas cooled to 5° C.
  4. filtrationthe formed precipitate was filtered
  5. washwashed with cool water

Sources & evidence

ORD record
ord-050e169340b0419bbefac74f7b2764f9
Source dataset
uspto-grants-1979_09
Patent number
US04168313

Reaction notes

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