Phenol → Phenyl acridine-9-carboxylate

HRID 2395921노트

반응식

HRID 2395921 반응식
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[C:15]([OH:17])=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:24]1(O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>S(Cl)(Cl)=O.C(Cl)Cl>[CH:11]1[C:12]2[C:7](=[N:6][C:5]3[C:14]([C:13]=2[C:15]([O:17][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:16])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

참가 물질

6

반응물 3

HCID 996PhenolHCID 1049PyridineHCID 94721Acridine-9-carboxylic acid

생성물 1

HCID 517916Phenyl acridine-9-carboxylate

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 24386Thionyl Chloride용매

실험 절차

Acridine-9-carboxylic acid (1 g, 4.1 mmol) was suspended in thionyl chloride (5 mL) and the reaction mixture was refluxed for 3 hours. The solvent was removed under reduced pressure leaving a yellow solid which was dissolved in methylene chloride and pyridine (350 μL) under argon. This solution was cooled in an ice bath and a solution of phenol (0.78 g, 8.2 mmol) in methylene chloride was added dropwise. The reaction mixture was stirred overnight at room temperature. After evaporation of solvent, the residue was redissolved in ethyl acetate and washed with water. The organic layer was dried over MgSO4 and concentrated to obtain a crudematerial which was chromatographed on silica gel (30% ethyl acetate/hexane)to yield the pure product as a yellow solid. 1H NMR (CDCl3) δ7.35-7.57 (m, 5H), 7.63-8.37 (m, 8H).

후처리

  1. temperaturethe reaction mixture was refluxed for 3 hours
  2. customThe solvent was removed under reduced pressure
  3. customleaving a yellow solid which
  4. temperatureThis solution was cooled in an ice bath
  5. customAfter evaporation of solvent
  6. dissolutionthe residue was redissolved in ethyl acetate
  7. washwashed with water
  8. dry with materialThe organic layer was dried over MgSO4
  9. concentrationconcentrated
  10. customto obtain a crudematerial which
  11. customwas chromatographed on silica gel (30% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-18073fa1fa044b4ba7e65bd405adcda3
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05491072

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