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Water → 2-(4-Chlorophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carboxylic acid

HRID 2272257
Notes
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Reaction equation

HRID 2272257 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]#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.[OH2:25].[OH-:26].[Na+]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]([OH:26])=[O:25])=[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 866989972-(4-Chlorophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carbonitrile

Product 1

HCID 866989982-(4-Chlorophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of (v) (20 g, 0.06 mol) in EtOH:water (400 ml, 1:1 v/v) was added NaOH (59.0 g, 0.02 mol) and the reaction mixture heated at 90° C. for 15 h. The reaction was then cooled to RT and the volatiles were removed in vacuo. The residual aqueous solution was acidified to pH 2 with aq. 2N HCl solution whereupon a solid precipitated from solution. The solid was separated by filtration and dissolved in EtOAc (300 mL), dried (Na2SO4) and concentrated in vacuo to give (vi) (7.5 g, with purity 75% by HPLC analysis). The material was used unpurified in subsequent steps.

Workup

  1. temperatureThe reaction was then cooled to RT
  2. customthe volatiles were removed in vacuo
  3. customprecipitated from solution
  4. customThe solid was separated by filtration
  5. dissolutiondissolved in EtOAc (300 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c4f477053676409f880aeace56dd5cbd
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09120775B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes