Acetic Anhydride → 1-Acetyl-5-iodo-6-methylindazole

HRID 13068

Reaction equation

HRID 13068 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[CH3:8][C:9]1[CH:15]=[C:14]([I:16])[C:13]([CH3:17])=[CH:12][C:10]=1[NH2:11].C([O-])(=O)C.[K+].C(O[N:29]=O)CC(C)C>C1C=CC=CC=1>[C:5]([N:11]1[C:10]2[C:9](=[CH:15][C:14]([I:16])=[C:13]([CH3:17])[CH:12]=2)[CH:8]=[N:29]1)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8053Isoamyl NitriteHCID 517044Potassium AcetateHCID 4770984(4-Iodo-2,5-Dimethylphenyl)Amine

Product 1

HCID 593397351-Acetyl-5-iodo-6-methylindazoleYield 21%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

Acetic acid anhydride (6.9 mL, 72 mmol) was added to a slurry of 2,5-dimethyl-4-iodoaniline (6.0 g, 24 mmol) and potassium acetate (2.4 g, 24 mmol) in benzene (50 mL). The mixture was heated to 80° C. and isopentylnitrit (4.8 mL, 36 mmol) was added during 20 min. The mixture was stirred at 80° C. overnight, then cooled and filtered. The filtrate was evaporated and purified by column chromatography (SiO2, dichloromethane). Product containing fractions were pooled and concentrated. The subtitle compound (1.5 g, 21%) was obtained as crystals from ethyl acetate.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. custompurified by column chromatography (SiO2, dichloromethane)
  5. additionProduct containing fractions
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-15ee512a6807457dac01a4e09db860ab
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Linked notes

Loading…