p-Aminoacetophenone → Ethanone, 1-(4-amino-3-iodophenyl)-

HRID 885926Notes

Reaction equation

HRID 885926 reaction equation
C([O-])([O-])=O.[Ca+2].[C:6]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)(=[O:8])[CH3:7].[I:16]Cl>O.CO.CCOCC>[NH2:13][C:12]1[CH:14]=[CH:15][C:9]([C:6](=[O:8])[CH3:7])=[CH:10][C:11]=1[I:16]

Participants

7

Reactant 3

HCID 7468p-AminoacetophenoneHCID 10112Calcium CarbonateHCID 24640Iodine chloride

Product 1

HCID 11032652Ethanone, 1-(4-amino-3-iodophenyl)-Yield 44.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred suspension of CaCO3 (4.5 g, 45.27 mmol) in H2O (15 mL) was added a solution of 4-acetylaniline (4.1 g, 30.18 mmol) in MeOH (25 mL), followed by a solution of iodine monochloride (5.2 g, 31.88 mmol) in MeOH (20 mL) dropwise. The reaction was stirred at r.t. for 45 minutes, then diluted with Et2O (150 mL). The organic fraction was separated, washed with water (100 mL), then brine (100 mL), dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (3.5 g, 44%) as a brown oil that was used without further purification. δH (DMSO-d6) 8.14 (1H, d, J 1.8 Hz), 7.70 (1H, dd, J 8.3 and 1.8 Hz), 6.75 (1H, d, J 8.3 Hz), 6.10 (2H, s), 2.41 (3H, s). LCMS (ES+) 261 (M)+, 283 (M+Na)+, RT 3.026 minutes (Method 5).

Workup

  1. customThe organic fraction was separated
  2. washwashed with water (100 mL)
  3. dry with materialbrine (100 mL), dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7479d65ae27a4ec8b019a22d89d086b0
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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