Acetic Acid → 9-Bromo-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetic acid

HRID 1384821노트

반응식

HRID 1384821 반응식
[Br:1][C:2]1[C:3]2[C:4]3[C:15](CC#N)=[N:14][N:13]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:12](=[O:25])[C:5]=3[N:6]([CH3:11])[C:7]=2[CH:8]=[CH:9][CH:10]=1.Cl.[C:27]([OH:30])(=[O:29])[CH3:28]>>[Br:1][C:2]1[C:3]2[C:4]3[C:15]([CH2:28][C:27]([OH:30])=[O:29])=[N:14][N:13]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:12](=[O:25])[C:5]=3[N:6]([CH3:11])[C:7]=2[CH:8]=[CH:9][CH:10]=1

참가 물질

4

반응물 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 211837399-Bromo-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetonitrile

생성물 1

HCID 211837259-Bromo-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetic acid

실험 절차

A solution of 4.8 g (12.2 mmol) of 9-bromo-5-methyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetonitrile in a mixture of 190 ml of acetic acid and of 50 ml of concentrated hydrochloric acid is heated at reflux for 6 h. The solution is concentrated under reduced pressure and the residue is taken up in a mixture of dichloromethane and of water. Basification is carried out with 30% sodium hydroxide solution, separation is carried out by settling and extraction is carried out with dichloromethane. The aqueous phase is acidified with concentrated hydrochloric acid while cooling with an ice bath. The precipitate is collected by filtration, washed with water and dried under reduced pressure. 3.1 g (7.5 mmol) of solid are obtained.

후처리

  1. temperatureat reflux for 6 h
  2. concentrationThe solution is concentrated under reduced pressure
  3. additionthe residue is taken up in a mixture of dichloromethane and of water
  4. customBasification is carried out with 30% sodium hydroxide solution, separation
  5. extractionextraction
  6. temperaturewhile cooling with an ice bath
  7. filtrationThe precipitate is collected by filtration
  8. washwashed with water
  9. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-bad266f6fea24d97b70184279ff7acc1
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06262045B1

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