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

HRID 1037524노트

반응식

HRID 1037524 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-8cba4bb1f3c0476b89a3b81eac0682fa
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546389B2

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