Citric Acid → 3,4,5-Trimethoxy-N-methycinnamohydroxamic acid

HRID 620404

반응식

HRID 620404 반응식
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:18]=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22])[CH:13]=[CH:14][C:15](O)=[O:16].ClC(OCC)=O.Cl.[CH3:32][NH:33][OH:34].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:18]=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22])[CH:13]=[CH:14][C:15]([N:33]([CH3:32])[OH:34])=[O:16]

참가 물질

7

반응물 5

HCID 311Citric AcidHCID 70213-(3,4,5-Trimethoxyphenyl)acrylic acidHCID 8471Triethylamine2회HCID 10928Ethyl chloroformateHCID 77906N-methylhydroxylamine hydrochloride

생성물 1

HCID 855991123,4,5-Trimethoxy-N-methycinnamohydroxamic acid수율 34%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
-12 °C

실험 절차

Triethylamine (3.07 ml, 22 mmol) was added to a stirred solution of 3,4,5-trimethoxycinnamic acid (4.76 g, 20 mmol) in N,N-dimethylformamide (30 ml). The resulting solution was cooled to -12° C., and ethyl chloroformate (2.00 ml, 21 mmol) was added dropwise with stirring. After 15 minutes, solid N-methylhydroxylamine hydrochloride (1.84 g, 22 mmol) was added, followed by triethylamine (3.2 ml, 23 mmol). The mixture was allowed to warm to room temperature, stirred overnight, and poured into 150 ml of 1% aqueous citric acid. The mixture was extracted twice with ethyl ether, and the combined extracts washed successively with water and brine, then dried over MgSO4, filtered, and evaporated. The residue was recrystallized from ethyl acetate to provide 1.82 g (34% yield) of the titled compound as colorless crystals, mp 169°-170° C.

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. extractionThe mixture was extracted twice with ethyl ether
  4. washthe combined extracts washed successively with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-3701ffc56a7f42ecb653d82459bf55ba
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04820828

연결된 노트

불러오는 중…