Acetic Anhydride → 1-(5-Bromo-3-methyl-1H-indazol-1-yl)ethan-1-one

HRID 1988910Notes

Reaction equation

HRID 1988910 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH2:9][CH3:10])[CH:3]=1.[C:11]([O-:14])(=O)[CH3:12].[K+].C(OC(=O)C)(=O)C.C1OCCOCCOCCOCCOCCOC1.C(O[N:46]=O)(C)(C)C>C(Cl)(Cl)Cl>[C:11]([N:6]1[C:5]2[C:4](=[CH:3][C:2]([Br:1])=[CH:8][CH:7]=2)[C:9]([CH3:10])=[N:46]1)(=[O:14])[CH3:12]

Participants

7

Reactant 5

HCID 7918Acetic AnhydrideHCID 10906Tert-Butyl nitriteHCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 28012834-Bromo-2-ethylaniline

Product 1

HCID 591273821-(5-Bromo-3-methyl-1H-indazol-1-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 4-bromo-2-ethylaniline (1.09 g) in chloroform (20 ml) was stirred at room temp. then treated with potassium acetate (0.49 g) followed by acetic anhydride (0.95 ml). 18-Crown-6 (0.26 g) and t-butylnitrite (1.32 ml) were added after 30 min and the mixture was stirred at reflux for 18 h. The reaction mixture was diluted with chloroform and washed with saturated aqueous sodium hydrogen carbonate. The organic phase was separated using a hydrophobic frit and the solvent was evaporated to give the title compound as a brown solid (1.0 g).

Workup

  1. temperatureat reflux for 18 h
  2. washwashed with saturated aqueous sodium hydrogen carbonate
  3. customThe organic phase was separated
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c1fb128394264464bf83d4b429327bb3
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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