2-Amino-5-chlorobenzoic acid → N-(3,4-dimethoxycinnamoyl)-5-chloroanthranilic acid

HRID 1156853

반응식

HRID 1156853 반응식
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([NH2:11])=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH:17]=[CH:18][C:19](Cl)=[O:20]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH:17]=[CH:18][C:19]([NH:11][C:5]1[C:6](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:7]([OH:9])=[O:8])=[O:20]

참가 물질

5

반응물 2

HCID 124762-Amino-5-chlorobenzoic acidHCID 533992063,4-Dimethoxycinnamoylchloride

생성물 1

HCID 54036349N-(3,4-dimethoxycinnamoyl)-5-chloroanthranilic acid수율 43.2%

시약·촉매·용매 2

HCID 6212Chloroform용매2회HCID 8471Triethylamine용매

실험 절차

In a mixture of 30 ml of chloroform and 3 ml of triethylamine is dissolved 3.4 g of 5-chloroanthranilic acid. To this solution is added a solution of 4.5 g of 3,4-dimethoxycinnamoylchloride in chloroform, and the mixture is heated under reflux for 2 hours. The reaction mixture is concentrated under a reduced pressure, and to the residue is added water and hydrochloric acid then added to make the mixture weakly acidic. The precipitated crystals are collected by filtration and recrystallized from ethanol to obtain 3.1 g of N-(3,4-dimethoxycinnamoyl)-5-chloroanthranilic acid as pale yellow needles.

후처리

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction mixture is concentrated under a reduced pressure
  4. additionto the residue is added water and hydrochloric acid
  5. additionthen added
  6. filtrationThe precipitated crystals are collected by filtration
  7. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-c73fa068b6df462781de51a9b738a5a4
출처 데이터셋
uspto-grants-1982_06
특허 번호
US04337270

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