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

HRID 437199

반응식

HRID 437199 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 23978Copper촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-501d62bb9d4e4449a8998af01be37226
출처 데이터셋
uspto-grants-1977_06
특허 번호
US04029815

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