Nitric Acid → Ethyl 5-nitro-1H-indazole-3-carboxylate

HRID 747101

反応式

HRID 747101 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:2]1.[N+:15]([O-])([OH:17])=[O:16]>S(=O)(=O)(O)O>[N+:15]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][N:2]=[C:3]2[C:10]([O:12][CH2:13][CH3:14])=[O:11])([O-:17])=[O:16]

参加物

4

反応物 2

HCID 944Nitric AcidHCID 78251ethyl 1H-indazole-3-carboxylate

生成物 1

HCID 12689368Ethyl 5-nitro-1H-indazole-3-carboxylate収率 53%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒2 回

反応条件

温度
0 °C

実験手順

Ethyl indazole-3-carboxylate (73.7 mmol) was dissolved in 20 mL concentrated sulfuric acid and the reaction mixture was cooled to 0° C. A mixture of concentrated sulfuric acid (12 mL) and 70% nitric acid (12 mL) was added dropwise over the course of 1 h. The mixture was stirred for an additional 1 h at 0° C. and was poured onto of crushed ice (200 g). The solid was collected by vacuum filtration, washed with several portions of water and dried in vacuo. The dried solid was suspended in 250 mL acetonitrile and the mixture was heated at reflux for 2 h. The mixture was allowed to cool to room temperature and the solid was collected and dried in vacuo to provide ethyl 5-nitroindazole-3-carboxylate (53%) as a colorless solid. The acid, obtained by basic hydrolysis, was coupled with the bicyclobase according to procedure A.

後処理

  1. additionwas added dropwise over the course of 1 h
  2. filtrationThe solid was collected by vacuum filtration
  3. washwashed with several portions of water
  4. customdried in vacuo
  5. temperaturethe mixture was heated
  6. temperatureat reflux for 2 h
  7. temperatureto cool to room temperature
  8. customthe solid was collected
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-c61aef33cfe44b9bbabc0cfb772115d7
出典データセット
uspto-grants-2008_07
特許番号
US07396833B2

関連ノート

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