Borane → HCID 20488239, 화합물

HRID 1995349노트

반응식

HRID 1995349 반응식
[CH3:1][N:2]([CH3:18])[C:3]([C:5]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:9][NH:8][C:7](=[O:17])[CH:6]=1)=O.B.[OH-].[Na+]>O1CCCC1>[CH3:18][N:2]([CH2:3][C:5]1[C:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[N:9][NH:8][C:7](=[O:17])[CH:6]=1)[CH3:1]

참가 물질

5

반응물 3

HCID 6331BoraneHCID 14798Sodium HydroxideHCID 20488245HCID 20488245, 화합물

생성물 1

HCID 20488239HCID 20488239, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

2,3-Dihydro-3-oxo-6-phenyl-5-pyridazinecarboxylic acid is treated with ethyl chloroformate, triethylamine, and dimethylamine according to the procedure of Example 3 to give N,N-dimethyl-2,3-dihydro-3-oxo-6-phenyl-5-pyridazinecarboxamide. A solution of this amide (12.5 g) in 400 ml of tetrahydrofuran is treated with 100 ml of 1 M borane in tetrahydrofuran and the resulting mixture is heated under reflux for 4 hours, then cooled and treated with 5% sodium hydroxide (100 ml) and heated under reflux for 1 hour. The tetrahydrofuran is removed on the rotary evaporator and the pH of the residual liquid is adjusted with acetic acid followed by ammonium hydroxide to 10. The product is extracted into dichloromethane and the dichloromethane is filtered and concentrated on the rotary evaporator. The residue is chromatographed on silica gel with 2% methanol and chloroform to give 5-(dimethylaminomethyl)-6-phenyl-3(2H)-pyridazinone.

후처리

  1. temperaturethe resulting mixture is heated
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. temperatureheated
  5. temperatureunder reflux for 1 hour
  6. customThe tetrahydrofuran is removed on the rotary evaporator
  7. extractionThe product is extracted into dichloromethane
  8. filtrationthe dichloromethane is filtered
  9. concentrationconcentrated on the rotary evaporator
  10. customThe residue is chromatographed on silica gel with 2% methanol and chloroform

출처 및 근거

ORD 기록
ord-4a088dbc6f2c40879c7548761859377e
출처 데이터셋
uspto-grants-1983_09
특허 번호
US04404203

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