Acetic Acid → 4-(3-Cyclopropylmethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-benzonitrile

HRID 602408Notes

Reaction equation

HRID 602408 reaction equation
[CH:1]1([CH2:4][C:5]([CH:7]2[C:12](=O)[CH2:11][C:10]([CH3:15])([CH3:14])[CH2:9][C:8]2=[O:16])=O)[CH2:3][CH2:2]1.Cl.[C:18]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][NH2:27])=[CH:22][CH:21]=1)#[N:19].CC(O)=O>CCO>[CH:1]1([CH2:4][C:5]2[C:7]3[C:8](=[O:16])[CH2:9][C:10]([CH3:15])([CH3:14])[CH2:11][C:12]=3[N:26]([C:23]3[CH:24]=[CH:25][C:20]([C:18]#[N:19])=[CH:21][CH:22]=3)[N:27]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 162129624-Cyanophenylhydrazine HydrochlorideHCID 441904592-(2-Cyclopropylacetyl)-5,5-dimethylcyclohexane-1,3-dione

Product 1

HCID 669524354-(3-Cyclopropylmethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-benzonitrileYield 51.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-Cyclopropyl-acetyl)-5,5-dimethyl-cyclohexane-1,3-dione (111.1 mg, 0.5 mmol) and 4-cyanophenylhydrazine hydrochloride (84.8 mg, 0.5 mmol, 1.0 eq) were suspended in 4 mL of 3:1 EtOH:AcOH and microwaved at 100° C. for 10 minutes. The solvent was removed in vacuo and the resultant residue purified by column chromatography to yield 81.8 mg (51% yield) of 4-(3-Cyclopropylmethyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-benzonitrile as an off-white powder.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resultant residue purified by column chromatography

Sources & evidence

ORD record
ord-33788ce07e3944a4a81c2413730dcb68
Source dataset
uspto-grants-2011_03
Patent number
US07906529B2

Reaction notes

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