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

HRID 48188

반응식

HRID 48188 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 23978Copper촉매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-25156da413f74e3fb251e988748786fe
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703388B2

연결된 노트

불러오는 중…