Ethanol → 2-(4-bromophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carboxylic acid

HRID 1037524ノート

反応式

HRID 1037524 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2C(C#N)=[C:15]3[C:10]([CH:11]=[C:12]([N+:22]([O-:24])=[O:23])[C:13]([CH:19]4[CH2:21][CH2:20]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.[OH-:25].[Na+].[CH2:27]([OH:29])[CH3:28]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:28]([C:27]([OH:25])=[O:29])=[C:15]3[C:10]([CH:11]=[C:12]([N+:22]([O-:24])=[O:23])[C:13]([CH:19]4[CH2:21][CH2:20]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 675140672-(4-bromophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carbonitrile

生成物 1

HCID 677745202-(4-bromophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carboxylic acid収率 63%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

To a stirred suspension of compound (vi) (3.3 g, 8.6 mmol) in ethanol (35 mL) was added aqueous NaOH (3.44 g, 86 mmol) and the reaction mixture was heated to 90° C. and maintained for 15 h when TLC and LCMS showed the absence of SM and formation of product. Concentration of the solvent gave a crude residue which was dissolved in water and filtered. The filtrate was acidified with dilute HCl at which time the product precipitated and was filtered to give the crude product which was purified by acid-base treatment to give 2-(4-bromophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carboxylic acid (vii) (2.2 g, 63%).

後処理

  1. temperaturemaintained for 15 h when TLC and LCMS
  2. customConcentration of the solvent gave a crude residue which
  3. filtrationfiltered
  4. customprecipitated
  5. filtrationwas filtered
  6. customto give the crude product which
  7. customwas purified by acid-base treatment

出典と根拠

ORDレコード
ord-8cba4bb1f3c0476b89a3b81eac0682fa
出典データセット
uspto-grants-2013_10
特許番号
US08546389B2

反応ノート

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