Anthranilic Acid → N-(3',4'-dimethoxycinnamoyl)anthranilic acid

HRID 1588959노트

반응식

HRID 1588959 반응식
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[Cl-].[Mg+2].[Cl-].S(Cl)(Cl)=O.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28](O)=[O:29])=[CH:22][C:21]=1[O:31][CH3:32]>O.CN(C)C=O>[CH3:32][O:31][C:21]1[CH:22]=[C:23]([CH:24]=[CH:25][C:20]=1[O:19][CH3:18])[CH:26]=[CH:27][C:28]([NH:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([OH:10])=[O:9])=[O:29]

참가 물질

7

반응물 4

HCID 227Anthranilic AcidHCID 24386Thionyl ChlorideHCID 7175313,4-Dimethoxycinnamic acidHCID 5360315Magnesium Chloride

생성물 1

HCID 5527N-(3',4'-dimethoxycinnamoyl)anthranilic acid수율 75.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

Into 15 ml of dimethylformamide were dissolved with heating 2.06 g (0.015 mol) of anthranilic acid and 2.7 g of magnesium chloride (anhydrous), and the resulting solution was cooled to room temperature. To 10 ml of dimethylformamide were added in order 0.78 ml of thionyl chloride and 2.08 g (0.01 mol) of 3',4'-dimethoxycinnamic acid, during which the reaction system was stirred and cooled with ice and water. After being stirred for additional 15 minutes, the resulting mixture was added dropwise to the above solution, with stirring at room temperature. After the completion of the dropping. the reaction mixture was stirred for additional 1.5 hours, and then treated in the same manner as in Example 2. There was obtained 2.48 g (yield: 75.8%) of N-(3',4'-dimethoxycinnamoyl)-anthranilic acid. Melting point: 209°-211° C.

후처리

  1. stirringAfter being stirred for additional 15 minutes
  2. additionthe resulting mixture was added dropwise to the above solution
  3. stirringwith stirring at room temperature
  4. stirringthe reaction mixture was stirred for additional 1.5 hours
  5. additiontreated in the same manner as in Example 2

출처 및 근거

ORD 기록
ord-9535f1528d5543f78b3e2287c8f7ad79
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05223639

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