3-(Trifluoromethyl)aniline → Talniflumate

HRID 127359Notes

Reaction equation

HRID 127359 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].Cl[C:13]1[C:18]([C:19]([O:21][CH:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:24](=[O:25])[O:23]2)=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=1>C1(C)C(C)=CC=CC=1>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH:6][C:13]1[C:18]([C:19]([O:21][CH:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:24](=[O:25])[O:23]2)=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

4

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 12673421Phthalidyl 2-chloro-3-pyridinecarboxylate

Product 1

HCID 48229TalniflumateYield 82.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To 80 ml of xylene, under reflux, m-trifluoromethylaniline (32.2 g) is added. Then, 29 g of phthalidyl 2-chloro-3-pyridinecarboxylate prepared in accordance with Example 1, Supra (divided in two fractions) is poured into the mixture with an interval of 15 minutes between each addition. The reaction mixture so obtained is maintained under reflux for 5 hours, and then cooled by pouring the mixture into an ice/water bath. To allow the complete crystallization of the desired product, the poured reaction mixture is maintained for 2 hours at a temperature of 0°-5° C. The precipitate is collected by filtration and dried under vacuum, at a temperature of 40° C. A yield of 34.1 g (82.3% of theory) of phthalidyl 2-(3-trifluoromethylanilino)-3-pyridinecarboxylate is obtained (m.p. 159°-162° C.). Recrystallizing the compound with 6 volumes of ethyl acetate, 28.4 g (68.5% yield) is obtained (m.p. 164°-5° C.).

Workup

  1. additionis poured into the mixture with an interval of 15 minutes between each addition
  2. customThe reaction mixture so obtained
  3. temperatureis maintained
  4. temperatureunder reflux for 5 hours
  5. temperaturecooled
  6. additionby pouring the mixture into an ice/water bath
  7. customthe complete crystallization of the desired product
  8. customthe poured reaction mixture
  9. temperatureis maintained for 2 hours at a temperature of 0°-5° C
  10. filtrationThe precipitate is collected by filtration
  11. customdried under vacuum, at a temperature of 40° C

Sources & evidence

ORD record
ord-30bdcc9f58504e3f887c20d9029bc84a
Source dataset
uspto-grants-1981_03
Patent number
US04255581

Reaction notes

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