Acetic Anhydride → 4-Methyl-1H-indazole-5-carbonitrile
Reaction equation
C(OC(=O)C)(=O)C.C([O-])(=O)C.[K+].[N:13](OCCC(C)C)=O.[C:21]([C:23]1[CH:28]=[CH:27][C:26]([NH:29]C(=O)C)=[C:25]([CH3:33])[C:24]=1[CH3:34])#[N:22]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH3:34][C:24]1[C:23]([C:21]#[N:22])=[CH:28][CH:27]=[C:26]2[C:25]=1[CH:33]=[N:13][NH:29]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Acetic anhydride (2.1 ml, 22.3 mmol), tetra-n-butylammonium bromide (118 mg, 0.366 mmol), potassium acetate (1.44 g, 14.7 mmol) and isoamyl nitrite (1.3 ml, 9.68 mmol) were added to an ethyl acetate suspension (15 ml) of N-(4-cyano-2,3-dimethylphenyl)acetamide (1.38 g, 7.33 mmol) at room temperature, and then the reaction was carried out for 7 hours under reflux conditions. The reaction mixture was cooled, diluted with ethyl acetate, and then washed with a saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and then distilled to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: n-hexane/chloroform) to obtain 4-methyl-1H-indazole-5-carbonitrile (1.24 g, 84.9%).
Workup
- temperatureThe reaction mixture was cooled
- washwashed with a saturated aqueous sodium hydrogencarbonate solution
- washThe organic layer was washed with a saturated aqueous sodium chloride solution
- dry with materialdried over magnesium sulfate
- distillationdistilled
- customto remove the solvent
- customthe resulting residue was purified by a silica gel column chromatography (eluent: n-hexane/chloroform)
Sources & evidence
- ORD record
- ord-e5d17bafa4224391a536eb3d486caa10
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199147B2
Reaction notes
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