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

HRID 1919595Notes

Reaction equation

HRID 1919595 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 4).

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-eea59f3c349b4ae396481a41ffc5b60e
Source dataset
uspto-grants-2012_05
Patent number
US08168634B2

Reaction notes

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