Ethyl Acetate → 7-Hydroxycarbostyril

HRID 1655023ノート

反応式

HRID 1655023 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](Cl)(=[O:18])[CH:10]=[CH:11]C1C=CC=CC=1.CCOC(C)=O>C(Cl)Cl.N1C=CC=CC=1>[OH:8][C:4]1[CH:3]=[C:2]2[C:7]([CH:11]=[CH:10][C:9](=[O:18])[NH:1]2)=[CH:6][CH:5]=1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 115683-AminophenolHCID 660233-Phenylprop-2-enoyl chloride

生成物 1

HCID 109757877-Hydroxycarbostyril

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 3-aminophenol (1 g) in CH2Cl2 (25 mL) and pyridine (1 mL) at 5° C. was added dropwise a solution of cinnamoyl chloride (1.53 g) in CH2Cl2 (10 mL). The mixture was warmed to r.t. over 1 hr, and then EtOAc (150 mL) was added. The organics were washed with H2O, 1N, HCl, saturated aq. NaHCO3 and H2O, dried (MgSO4) and concentrated. To the residue was added AlCl3 (6.38 g) and the mixture heated at 180° C. for 5 min. and then at 115°-120° C. for 2 hr. To the mixture was added ice and then H2O. The solid that formed was collected by filtration, washed with 2N HCl and H2O (3×). The resulting solid was triturated in EtOAc to provide the title compound.

後処理

  1. washThe organics were washed with H2O, 1N, HCl, saturated aq. NaHCO3 and H2O
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. additionTo the residue was added AlCl3 (6.38 g)
  5. temperaturethe mixture heated at 180° C. for 5 min.
  6. additionTo the mixture was added ice
  7. customThe solid that formed
  8. filtrationwas collected by filtration
  9. washwashed with 2N HCl and H2O (3×)
  10. customThe resulting solid was triturated in EtOAc

出典と根拠

ORDレコード
ord-84bcab8d5fb54118a5f5807ebd975af0
出典データセット
uspto-grants-1995_04
特許番号
US05410054

反応ノート

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