Iodine → HCID 86680194, compound

HRID 2402344Notes

Reaction equation

HRID 2402344 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([CH:14]([CH3:16])[CH3:15])=[CH:10][C:11]([O-:13])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[Mg].II.[Cl-].[NH4+].[CH3:22]O>>[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:14]([CH3:16])[CH3:15])[CH2:10][C:11]([O:13][CH3:22])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 5

HCID 807IodineHCID 887MethanolHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 86680195HCID 86680195, compound

Product 1

HCID 86680194HCID 86680194, compound

Conditions

Temperature
60 °C

Procedure

At RT, a solution of 6.77 g (26.7 mmol) of methyl 2E/Z)-3-(3-amino-4-chlorophenyl)-4-methylpent-2-enoate in 130 ml of methanol was added to 2.2 g (90.7 mmol) of magnesium turnings and a few grains of iodine. After about 30 min, the internal temperature increased to about 60° C. After the reaction solution had cooled to room temperature, stirring at room temperature was continued for another 2 h. 50 ml of saturated aqueous ammonium chloride solution were then added slowly to the dark reaction mixture, and the mixture was extracted repeatedly with diethyl ether. The combined organic phases were washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. The residue obtained was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 2.95 g (40% of theory) of the title compound as an oil.

Workup

  1. temperatureAfter the reaction solution had cooled to room temperature
  2. waitwas continued for another 2 h
  3. extractionthe mixture was extracted repeatedly with diethyl ether
  4. washThe combined organic phases were washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-78a35bca481042b0ab1e6291e1b01f99
Source dataset
uspto-grants-2014_08
Patent number
US08796335B2

Reaction notes

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