Dimethylformamide → 2-(Nitrophenyl)amino-3,4-dimethylbenzoic acid

HRID 48188

反応式

HRID 48188 の反応式
[CH3:1][C:2]1[C:3](I)=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[N+:13]([C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH2:18])([O-:15])=[O:14].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.[Cu]>[N+:13]([C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH:18][C:3]1[C:2]([CH3:1])=[C:10]([CH3:11])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])([O-:15])=[O:14]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 69462-NitroanilineHCID 11430Potassium CarbonateHCID 111966352-Iodo-3,4-dimethylbenzoic acid

生成物 1

HCID 227424482-(Nitrophenyl)amino-3,4-dimethylbenzoic acid収率 24.1%

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 962Water溶媒

実験手順

10 g of 3,4-dimethyl-2-iodobenzoic acid, 6 g of 2-nitroaniline, 250 mg of powdery copper and 25 g of potassium carbonate were added to N,N-dimethylformamide and heated under reflux while stirring for 2 hr. Then the reaction mixture was cooled to room temperature and diluted with water. After adjusting the pH value thereof to pH 4 with conc. hydrochloric acid, it was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography to give 2.5 g of the title compound.

後処理

  1. temperatureheated
  2. temperatureunder reflux
  3. extractionto pH 4 with conc. hydrochloric acid, it was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter evaporating the solvent under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-25156da413f74e3fb251e988748786fe
出典データセット
uspto-grants-2004_03
特許番号
US06703388B2

関連ノート

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