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Hydrazine hydrate (1:1) → 4-(4-Bromo-2-chlorophenylamino)-5-chloro-6-hydrazinonicotinic acid ethyl ester

HRID 917027
ノート
印刷プレビュー

反応式

HRID 917027 の反応式
BrC1C=CC(NC2C(C(O)=O)=CN=C(Cl)C=2Cl)=C(Cl)C=1.O.[NH2:22][NH2:23].[CH2:24]([O:26][C:27](=[O:45])[C:28]1[C:33]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([Br:41])=[CH:37][C:36]=2[Cl:42])=[C:32]([Cl:43])[C:31]([Cl:44])=[N:30][CH:29]=1)[CH3:25]>CN(C)C(=O)C.CCOC(C)=O>[CH2:24]([O:26][C:27](=[O:45])[C:28]1[C:33]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([Br:41])=[CH:37][C:36]=2[Cl:42])=[C:32]([Cl:43])[C:31]([Cl:44])=[N:30][CH:29]=1)[CH3:25].[CH2:24]([O:26][C:27](=[O:45])[C:28]1[C:33]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([Br:41])=[CH:37][C:36]=2[Cl:42])=[C:32]([Cl:43])[C:31]([NH:22][NH2:23])=[N:30][CH:29]=1)[CH3:25]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 24654Hydrazine hydrate (1:1)HCID 116612174-(4-Bromo-2-chlorophenylamino)-5,6-dichloronicotinic acidHCID 865967804-(4-Bromo-2-chlorophenylamino)-5,6-dichloronicotinic acid ethyl ester

生成物 2

HCID 688607444-(4-Bromo-2-chlorophenylamino)-5-chloro-6-hydrazinonicotinic acid ethyl ester収率 36.1%HCID 865967804-(4-Bromo-2-chlorophenylamino)-5,6-dichloronicotinic acid ethyl ester

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
90 °C

実験手順

4-(4-Bromo-2-chlorophenylamino)-5,6-dichloronicotinic acid ethyl ester (48) was prepared by standard methods from 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinic acid. Hydrazine monohydrate (0.59 mL, 12.16 mmol) was added to a solution of 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinic acid ethyl ester (48) (1.72 g, 4.05 mmol) in N,N-dimethylacetamide (20 mL). After stirring at 90° C. for 1 hour, the reaction mixture was cooled to room temperature and diluted with EtOAc. The organic layer was washed with water and brine, dried (Na2SO4) and concentrated. Purification by flash column chromatography using the Biotage system (20:1 CH2Cl2:EtOAc) provided the desired product (49) (307 mg, 18%).

後処理

  1. temperaturethe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by flash column chromatography

出典と根拠

ORDレコード
ord-4df591107a7348f7a4c0564bc75ff7eb
出典データセット
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07271178B2

反応ノート

読み込み中…

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