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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
ノート
印刷プレビュー

反応式

HRID 1031459 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1049PyridineHCID 759941-Benzylpiperazine2 回HCID 28744326-(4-chloro-3-nitrophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-67c3cefe31094c309bcfb63d75cbf5b8
出典データセット
uspto-grants-1990_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04954501

反応ノート

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