Chloroform → 2-Chloro-4-iodobenzylamine

HRID 551326Notes

Reaction equation

HRID 551326 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N:10]1C(=O)C2=CC=CC=C2C1=O.C(Cl)(Cl)Cl>C(O)C.O.NN>[Cl:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH2:9][NH2:10]

Participants

5

Conditions

Temperature
70 °C

Procedure

In a solution of 2.9 g of N-[(2-chloro-4-iodophenyl)methyl]phthalimide in 60 mL of ethanol, 3.0 mL of 80% hydrazine monohydrate aqueous solution was added, and stirred at 70° C. for 30 minutes. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, 100 mL of chloroform was added therein and insoluble substance was filtered off, and the solvent was distilled off under reduced pressure. The procedure comprising adding 30 mL of chloroform in the residue, filtering off insoluble material and distilling off the solvent under reduced pressure was repeated twice to obtain 2.8 g of the aimed product as yellow oily substance.

Workup

  1. customAfter the completion of the reaction
  2. waitthe reaction mixture was left
  3. temperaturecooled to room temperature
  4. filtrationinsoluble substance was filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionThe procedure comprising adding 30 mL of chloroform in the residue
  7. filtrationfiltering off insoluble material
  8. distillationdistilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-b266b9d6570a4cf398f60cc03f4b1d13
Source dataset
uspto-grants-2011_05
Patent number
US07947715B2

Reaction notes

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