Water → 1-Benzyl-3-cyclopropylindazol-6-ol

HRID 1873943Notes

Reaction equation

HRID 1873943 reaction equation
[CH:1]1([C:4]([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=2F)=O)[CH2:3][CH2:2]1.C([O-])(=O)C.[Na+].Cl.Cl.[CH2:21]([NH:28][NH2:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>C1(C)C(C)=CC=CC=1>[CH2:21]([N:28]1[C:7]2[C:6](=[CH:11][CH:10]=[C:9]([OH:12])[CH:8]=2)[C:4]([CH:1]2[CH2:3][CH2:2]2)=[N:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 146540Benzylhydrazine dihydrochlorideHCID 517045Sodium AcetateHCID 59370759Cyclopropyl(2-fluoro-4-hydroxyphenyl)methanone

Product 1

HCID 1358699421-Benzyl-3-cyclopropylindazol-6-ol

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Cyclopropyl(2-fluoro-4-hydroxyphenyl)methanone (6.51 g) which can be prepared according to the method described in Reference example 2, etc., sodium acetate (14.3163 g; manufactured by Wako Pure Chemical Industries, Ltd.), and benzylhydrazine-dihydrochloride (10.72 g; manufactured by Sigma-Aldrich Co.) were suspended in xylene (180 mL). By using a dean-stark apparatus, the mixture was stirred overnight at reflux. After cooling to room temperature, the mixture was added with water and extracted twice with ethyl acetate. The organic layer was washed twice with water and brine and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, insoluble matters were dissolved by adding n-hexane to the residue and the title compound was obtained as a crude product (10.97 g).

Workup

  1. temperatureat reflux
  2. extractionextracted twice with ethyl acetate
  3. washThe organic layer was washed twice with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter the solvent was evaporated under reduced pressure, insoluble matters
  6. dissolutionwere dissolved
  7. additionby adding n-hexane to the residue

Sources & evidence

ORD record
ord-e6d56046c6a6436a87da81b9d8fd5283
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

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