2,5-Dichlorobenzoic acid → 5-Chloro-2-[2-methyl-3-(trifluoromethyl)anilino]benzoic acid

HRID 437198

Reaction equation

HRID 437198 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(O)CCCC.[OH-].[Na+].[CH3:20][C:21]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:22]=1[NH2:23]>[Cu]>[Cl:11][C:8]1[CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]([NH:23][C:22]2[CH:24]=[CH:25][CH:26]=[C:27]([C:28]([F:29])([F:30])[F:31])[C:21]=2[CH3:20])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 57842,5-Dichlorobenzoic acidHCID 62761-PentanolHCID 14798Sodium HydroxideHCID 2735932Trifluoromethyl toluidine

Product 1

HCID 451177035-Chloro-2-[2-methyl-3-(trifluoromethyl)anilino]benzoic acid

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

To a solution of 25 g. of 2,5-dichlorobenzoic acid in 125 ml. of n-pentyl alcohol add 4.8 g. of sodium hydroxide pellets, 25 g. of 2-methyl-3-trifluoromethylaniline and 2 g. of copper powder. With constant stirring, reflux the reaction mixture for 18 hours. Concentrate the mixture to one half volume and dilute with water and ether. Acidify the aqueous layer to yield the product which is recrystallized from methanol, m.p. 220°-222° C.

Workup

  1. temperatureWith constant stirring, reflux the reaction mixture for 18 hours
  2. concentrationConcentrate the mixture to one half volume
  3. additiondilute with water and ether
  4. customto yield the product which
  5. customis recrystallized from methanol, m.p. 220°-222° C.

Sources & evidence

ORD record
ord-4d4f4c4afad6436984261a6ffd258e11
Source dataset
uspto-grants-1977_06
Patent number
US04029815

Linked notes

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