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

HRID 1451082ノート

反応式

HRID 1451082 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-04d8c2e88b7741e5b425dd1b33827c9e
出典データセット
uspto-grants-1997_02
特許番号
US05602277

反応ノート

読み込み中…