1-Pentanol → 2-[2-Methyl-3-(trifluoromethyl)anilino]-5-nitrobenzoic acid

HRID 437199

Reaction equation

HRID 437199 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(O)CCCC.[OH-].[Na+].[CH3:22][C:23]1[C:29]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:27]=[CH:26][C:24]=1[NH2:25]>[Cu]>[N+:11]([C:8]1[CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]([NH:25][C:24]2[CH:26]=[CH:27][CH:28]=[C:29]([C:30]([F:31])([F:32])[F:33])[C:23]=2[CH3:22])=[CH:10][CH:9]=1)([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 62761-PentanolHCID 14798Sodium HydroxideHCID 172872-Chloro-5-nitrobenzoic acidHCID 2735932Trifluoromethyl toluidine

Product 1

HCID 451177022-[2-Methyl-3-(trifluoromethyl)anilino]-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

To a solution of 25 g. of 2-chloro-5-nitro-benzoic 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 obtain a crude product which is recrystallized to yield 5-nitro-N-(2-methyl-3-trifluoromethylphenyl) anthranilic acid, m.p. 244°-245° 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 obtain a crude product which
  5. customis recrystallized

Sources & evidence

ORD record
ord-501d62bb9d4e4449a8998af01be37226
Source dataset
uspto-grants-1977_06
Patent number
US04029815

Linked notes

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