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

HRID 63528
Notes
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Reaction equation

HRID 63528 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-616b5a9e4eff4e59a5082410877cdea5
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447080B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes