Sodium Azide → 7-Azido-6-nitro-4-(3,4,5-trimethoxyanilino)-3-quinolinecarbonitrile

HRID 989299ノート

反応式

HRID 989299 の反応式
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:14][C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)=[C:7]([C:12]#[N:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:27]([O-:29])=[O:28].[N-:30]=[N+:31]=[N-:32].[Na+]>CS(C)=O>[N:30]([C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:14][C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)=[C:7]([C:12]#[N:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:27]([O-:29])=[O:28])=[N+:31]=[N-:32]

参加物

4

反応物 2

HCID 33557Sodium AzideHCID 21956430HCID 21956430、化合物

生成物 1

HCID 219564987-Azido-6-nitro-4-(3,4,5-trimethoxyanilino)-3-quinolinecarbonitrile収率 97.7%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
45 °C

実験手順

A mixture of 506.1 mg (1.2 mmol) of 7-chloro-6-nitro-4-(3,4,5-trimethoxyanilino)-3-quinolinecarbonitrile and 390.0 mg (6.0 mmol) of sodium azide in 10.0 mL of DMSO is heated at 40-50° C. for 5 hours, and then at room temperature for 15 hours. The mixture is poured into ice water and extracted with ethyl acetate. The organic phase is washed with brine and dried over sodium sulfate. Removal of the solvent yields 493.4 mg (97.7%) of 7-azido-6-nitro-4-(3,4,5-trimethoxyanilino)-3-quinolinecarbonitrile as a yellow solid which is used in the next reaction without further purification.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with brine
  3. dry with materialdried over sodium sulfate
  4. customRemoval of the solvent

出典と根拠

ORDレコード
ord-8fd3d16f4fc649f2ada8a83c4ef5cb59
出典データセット
uspto-grants-2003_10
特許番号
US06638929B2

反応ノート

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