Acetic Anhydride → HCID 23134654, compound

HRID 240760Notes

Reaction equation

HRID 240760 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.[C:10]([O:13]C(=O)C)(=O)[CH3:11].C([O-])(=O)C.[K+].C(O[N:28]=O)CC(C)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:7][CH:8]=1)[N:6]([C:10](=[O:13])[CH3:11])[N:28]=[CH:9]2

Participants

7

Reactant 5

HCID 7918Acetic AnhydrideHCID 8053Isoamyl NitriteHCID 832214-Iodo-o-toluidineHCID 516892Sodium BicarbonateHCID 517044Potassium Acetate

Product 1

HCID 23134654HCID 23134654, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
5 °C

Procedure

4-Iodo-2-methylaniline (30.2 g, 130 mmol) was dissolved in chloroform (300 mL) and cooled to 5° C. Acetic anhydride (35 mL, 343 mmol) was added dropwise, and the mixture was allowed to warm to ambient temperature. Potassium acetate (4.21 g, 42.9 mmol) and isoamylnitrite (37 mL, 277 mmol) were added, and the mixture was heated to 70° C. overnight. The mixture was neutralized with saturated aqueous sodium bicarbonate and extracted with methylene chloride. The solvents were removed under reduced pressure and the resulting residue was triturated with methanol to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.41 (s, 1H) 8.33 (s, 1H) 8.05-8.21 (m, 1H) 7.90 (dd, J=8.48, 1.70 Hz, 1H) 2.71 (s, 3H).

Workup

  1. temperatureto warm to ambient temperature
  2. temperaturethe mixture was heated to 70° C. overnight
  3. extractionextracted with methylene chloride
  4. customThe solvents were removed under reduced pressure
  5. customthe resulting residue was triturated with methanol

Sources & evidence

ORD record
ord-a2ec0fb688e94fc29c517e87c839fa5a
Source dataset
uspto-grants-2014_02
Patent number
US08648069B2

Reaction notes

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