4-Methyl-3-nitrobenzoic acid → N'-acetyl-4-methyl-3-nitrobenzohydrazide

HRID 1893543노트

반응식

HRID 1893543 반응식
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C(N(CC)CC)C.ClC(OCC(C)C)=O.[C:29]([NH:32][NH2:33])(=[O:31])[CH3:30]>C(OCC)(=O)C.ClCCl>[C:29]([NH:32][NH:33][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1)(=[O:31])[CH3:30]

참가 물질

7

반응물 4

HCID 73194-Methyl-3-nitrobenzoic acidHCID 8471TriethylamineHCID 14039AcetohydrazideHCID 62365Isobutyl chloroformate

생성물 1

HCID 47101699N'-acetyl-4-methyl-3-nitrobenzohydrazide수율 44%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

4-Methyl-3-nitrobenzoic acid (3.00 g, 16.5 mmol) was added to dichloromethane (50 ml), triethylamine (3.0 ml, 21.3 mmol) and isobutyl chloroformate (2.80 ml, 21.5 mmol) were added under ice-cooling with stirring, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was ice-cooled again, acetohydrazide (2.45 g, 33.1 mmol) was added with stirring, and the mixture was stirred at room temperature for about 3 hr. The reaction mixture was diluted with ethyl acetate, washed with 10% aqueous citric acid solution, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained solid was washed with diethyl ether and hexane to give the title compound (1.72 g, yield 44%) as a colorless solid.

후처리

  1. additionwere added under ice-
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 3 hr
  4. temperaturecooled again
  5. stirringwith stirring
  6. stirringthe mixture was stirred at room temperature for about 3 hr
  7. washwashed with 10% aqueous citric acid solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationThe insoluble material was filtered off
  10. concentrationthe solution was concentrated under reduced pressure
  11. washThe obtained solid was washed with diethyl ether and hexane

출처 및 근거

ORD 기록
ord-d2f3d1d6ab56494f99ed263bf1728d3b
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513235B2

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