Pyridine → Methyl 4-acetylamino-3-(2-hydroxyethoxy)benzoate

HRID 1451082노트

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HRID 1451082 반응식
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH2:13][CH2:14][OH:15].[C:16](OC(=O)C)(=[O:18])[CH3:17].N1C=CC=CC=1.C(OCC)(=O)C>ClCCl.O>[C:16]([NH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH2:13][CH2:14][OH:15])(=[O:18])[CH3:17]

참가 물질

7

반응물 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 10560441Methyl 4-amino-3-(2-hydroxyethoxy)benzoate

생성물 1

HCID 10491072Methyl 4-acetylamino-3-(2-hydroxyethoxy)benzoate수율 53%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To methyl 4-amino-3-(2-hydroxyethoxy)benzoate (2.98 g, 0.0141 mol) dissolved in dichloromethane (200 mL) was added acetic anhydride (1.49 mL, 0.0156 mol) and pyridine (1.34 mL, 0.0156 mol). After stirring for 3 h at room temperature, thin-layer chromatographic analysis (SiO2, ethyl acetate) showed disappearance of the starting material along with the appearance of a new lower-running spot (Rf =03) indicating the reaction was complete. The reaction was poured into water (70 mL) and the organic layer washed three times with water (50 mL). The organic layer was concentrated and then dried in vacuo. Thin-layer chromatographic analysis (SiO2, ethyl acetate) showed formation of some material as a higher-running spot (Rf =0.8) in addition to the product. Methanol (50 mL) and a catalytic amount of sodium methoxide was added to the residue. After 1 h, thin-layer chromatographic analysis (SiO2, ethyl acetate) showed only the desired product. The solution was neutralized with H+ resin, filtered, and then concentrated. The residue was recrystallized from ethyl acetate to give 1.88 g (53%) of methyl 4-acetylamino-3-(2-hydroxyethoxy)benzoate as an off-white solid.

후처리

  1. washthe organic layer washed three times with water (50 mL)
  2. concentrationThe organic layer was concentrated
  3. customdried in vacuo
  4. additionin addition to the product
  5. additionMethanol (50 mL) and a catalytic amount of sodium methoxide was added to the residue
  6. waitAfter 1 h
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-04d8c2e88b7741e5b425dd1b33827c9e
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05602277

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