2'-Aminoacetophenone → 1-(2-Amino-5-iodophenyl)ethan-1-one

HRID 1625709Notes

Reaction equation

HRID 1625709 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].C1C(=O)N([I:18])C(=O)C1>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([I:18])=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 110862'-AminoacetophenoneHCID 120273N-Iodosuccinimide

Product 1

HCID 590603631-(2-Amino-5-iodophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A flask charged with 1-(2-aminophenyl)ethanone (405 mg) and DCM (20 mL) was cooled in an ice/water bath and NIS (675 mg) was added in three portions. The reaction was stirred at 0° C. The reaction mixture was diluted with 30 mL DCM, washed with sat. aqueous NaHCO3, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by preparative RP-HPLC, affording the title compound. MS (ESI+): m/z 262.06 (MH+). 1H NMR (400 MHz, CDCl3): δ 7.94 (s, 1H), 7.44 (d, J=8.8 Hz, 1H), 6.43 (d, J=8.8 Hz, 1H), 6.32 (br, 2H), 2.53 (s, 3H).

Workup

  1. temperaturewas cooled in an ice/water bath
  2. washwashed with sat. aqueous NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-5ec60b7121fc4d0e80e487149145e91f
Source dataset
uspto-grants-2014_07
Patent number
US08785151B2

Reaction notes

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