Ethyl Acetate → 7-Hydroxycarbostyril

HRID 1655023노트

반응식

HRID 1655023 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 109757877-Hydroxycarbostyril

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-84bcab8d5fb54118a5f5807ebd975af0
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05410054

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