Sodium Hydroxide → 1,5,6,7-tetrahydro-4H-indazol-4-one

HRID 2366485Notes

Reaction equation

HRID 2366485 reaction equation
Cl.[NH2:2]N.[OH-].[Na+].C[N:7]([CH:9]=[C:10]1[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C:11]1=O)C>CO>[NH:2]1[C:11]2[CH2:12][CH2:13][CH2:14][C:15](=[O:16])[C:10]=2[CH:9]=[N:7]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 115031Hydrazinium chlorideHCID 3593532-[(Dimethylamino)methylidene]cyclohexane-1,3-dione

Product 1

HCID 101712471,5,6,7-tetrahydro-4H-indazol-4-oneYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to Scheme 1 Step 2: A solution of hydrazine hydrochloride (41.9 mmol, 2.87 g), NaOH (6 M, 42 mmol, 7.0 mL) in MeOH (100 mL) was added, at 0° C., to a solution of 2-((dimethylamino)methylene)cyclohexane-1,3-dione (41.9 mmol, 7.00 g) and the reaction mixture was stirred under reflux for 3 hours. After evaporation, water was added and the aqueous phase was extracted with AcOEt at 50° C. The organic phase was dried over Na2SO4, was filtered and was concentrated under reduced pressure to yield 6,7-dihydro-1H-indazol-4(5H)-one (36.7 mmol, 5.00 g, 88%) as a yellow powder.

Workup

  1. temperatureunder reflux for 3 hours
  2. customAfter evaporation, water
  3. additionwas added
  4. extractionthe aqueous phase was extracted with AcOEt at 50° C
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationwas filtered
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-fcbfe2f994c64798bfdc317706d89175
Source dataset
uspto-grants-2014_04
Patent number
US08697744B2

Reaction notes

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