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Pyridine → 6-[4-(4-benzyl-piperazin-1-yl)-3-nitro-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone

HRID 1031459
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HRID 1031459 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].[CH2:19]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1C=CC=CC=1>CN(C)C=O>[CH2:19]([N:26]1[CH2:31][CH2:30][N:29]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=3)=[CH:4][C:3]=2[N+:16]([O-:18])=[O:17])[CH2:28][CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1
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참가 물질

5

반응물 3

HCID 1049PyridineHCID 759941-Benzylpiperazine2회HCID 28744326-(4-chloro-3-nitrophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

생성물 1

HCID 144594646-[4-(4-benzyl-piperazin-1-yl)-3-nitro-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone수율 95.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

16.1 g (60 mmol) of 6-(4-chloro-3-nitro-phenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone, 15.9 g (90 mmol) of 1-benzyl-piperazine and 7.3 ml (90 mmol) of pyridine are stirred into 60 ml of dimethyl formamide at 100° C. A further 5.8 g (33 mmol) of 1-benzyl-piperazine is added after 7 hours and stirring of the reaction mixture is continued for 12 hours at 100° C. When the reaction mixture is cold it is poured out on 300 ml of ice water and the solid which precipitates is suction filtered. The aqueous phase is extracted twice with 200 ml of dichloromethane. The combined organic phases are washed with water and saturated sodium chloride solution, dried, filtered and concentrated by evaporation in vacuo. The solid residue obtained is recrystallized from 500 ml of ethanol together with the solid initially obtained. 23.4 g (95%) of orange red crystals melting at 220° to 221° C. are obtained.

후처리

  1. customthe solid which precipitates
  2. filtrationfiltered
  3. extractionThe aqueous phase is extracted twice with 200 ml of dichloromethane
  4. washThe combined organic phases are washed with water and saturated sodium chloride solution
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation in vacuo
  8. customThe solid residue obtained
  9. customis recrystallized from 500 ml of ethanol together with the solid
  10. custominitially obtained

출처 및 근거

ORD 기록
ord-67c3cefe31094c309bcfb63d75cbf5b8
출처 데이터셋
uspto-grants-1990_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04954501

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