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

HRID 437199

反応式

HRID 437199 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 23978Copper触媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-501d62bb9d4e4449a8998af01be37226
出典データセット
uspto-grants-1977_06
特許番号
US04029815

関連ノート

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