Acetic Anhydride → 1-Acetyl-4-bromo-1H-indazole
Reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:10]([O-:13])(=O)[CH3:11].[K+].C(OC(=O)C)(=O)C.[N:22](OCCC(C)C)=O>C1(C)C=CC=CC=1.O>[C:10]([N:5]1[C:4]2[C:3](=[C:2]([Br:1])[CH:8]=[CH:7][CH:6]=2)[CH:9]=[N:22]1)(=[O:13])[CH3:11]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To a mixture of 3-bromo-2-methylaniline (2.00 mL, 16.0 mmol) and potassium acetate (1.60 g, 16.3 mmol) in toluene (160 mL) was added acetic anhydride (4.54 mL, 48.0 mmol) at room temperature, and the mixture was stirred at 60° C. for 30 min. Isoamyl nitrite (3.22 mL, 24.0 mmol) was added, and the mixture was stirred at 60° C. for 18 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as a crudely purified product.
Workup
- stirringthe mixture was stirred at 60° C. for 18 hr
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-126306a822ef42aebf4668f9cc61b9c2
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08110585B2
Reaction notes
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