Benzylhydrazine dihydrochloride → 1-Benzyl-3-cyclobutylindazol-6-ol

HRID 1873947Notes

Reaction equation

HRID 1873947 reaction equation
[CH:1]1([C:5]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=2F)=O)[CH2:4][CH2:3][CH2:2]1.C([O-])(=O)C.[Na+].Cl.Cl.[CH2:22]([NH:29][NH2:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C(C)=CC=CC=1>[CH2:22]([N:29]1[C:8]2[C:7](=[CH:12][CH:11]=[C:10]([OH:13])[CH:9]=2)[C:5]([CH:1]2[CH2:4][CH2:3][CH2:2]2)=[N:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 146540Benzylhydrazine dihydrochlorideHCID 517045Sodium AcetateHCID 59370760HCID 59370760, compound

Product 1

HCID 1358699511-Benzyl-3-cyclobutylindazol-6-ol

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Cyclobutyl(2-fluoro-4-hydroxyphenyl)methanone (6.967 g) which can be prepared according to the method described in Reference example 9, etc., sodium acetate (14.16 g; manufactured by Kanto Chemical Co., Inc.), and benzylhydrazine-dihydrochloride (10.55 g; manufactured by Sigma-Aldrich Co.) were suspended in xylene (85 mL; manufactured by Wako Pure Chemical Industries, Ltd.). By using a dean-stark apparatus, the mixture was stirred overnight at reflux. After cooling to room temperature, solid obtained after filtering the precipitate was dissolved in water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate. The organic layer was combined, washed twice with water and brine and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the title compound was obtained (8.003 g).

Workup

  1. temperatureat reflux
  2. customsolid obtained
  3. filtrationafter filtering the precipitate
  4. dissolutionwas dissolved in water
  5. extractionThe aqueous layer was extracted twice with ethyl acetate
  6. washwashed twice with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customAfter the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7578d6dca10a4a5b960df9f8e8cf0be6
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

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