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Water → N-(3-Carboxyphenyl)-4-(3-furanyl)-2-nitroaniline

HRID 581951
ノート
印刷プレビュー

反応式

HRID 581951 の反応式
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[CH:14][O:13][CH:12]=2)=[CH:7][C:6]=1[N+:16]([O-:18])=[O:17])(=O)[CH3:2].I[C:20]1[CH:21]=[C:22](C=C[CH:28]=1)[C:23]([OH:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].O>CN1CCCC1=O>[C:23]([C:22]1[CH:2]=[C:1]([NH:4][C:5]2[CH:10]=[CH:9][C:8]([C:11]3[CH:15]=[CH:14][O:13][CH:12]=3)=[CH:7][C:6]=2[N+:16]([O-:18])=[O:17])[CH:28]=[CH:20][CH:21]=1)([OH:25])=[O:24]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 120603-Iodobenzoic acidHCID 54094756N-Acetyl 4-(3-furanyl)-2-nitroaniline

生成物 1

HCID 54219463N-(3-Carboxyphenyl)-4-(3-furanyl)-2-nitroaniline

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

A mixture of 1e from Example 19 (5 g, 24.5 mmol), 3-iodobenzoic acid (6.69 g, 27 mmol), potassium carbonate (3.79 g, 27.5 mmol) and a catalytic amount of copper-bronze in 30 ml dry N-methyl-2-pyrrolidone is heated to 180° C. overnight. After cooling water is added and the mixture is washed twice with ethyl acetate. The aqueous phase is rendered acidic with diluted hydrochloric acid and the oily precipitate is filtered off. This precipitate is extracted with ethyl acetate, and the extract is purified by column-chromatography on silica gel using a mixture of ethyl acetate and petroleum ether (1:1) as the eluent. Yield: 2.56 g (32%). Mp 203-205° C.

後処理

  1. additionis added
  2. washthe mixture is washed twice with ethyl acetate
  3. filtrationthe oily precipitate is filtered off
  4. extractionThis precipitate is extracted with ethyl acetate
  5. customthe extract is purified by column-chromatography on silica gel using
  6. additiona mixture of ethyl acetate and petroleum ether (1:1) as the eluent

出典と根拠

ORDレコード
ord-64b18ac42eef4ed4a22862b1edab773d
出典データセット
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05922724

反応ノート

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