Phthalimide → HCID 15391783, compound

HRID 394685Notes

Reaction equation

HRID 394685 reaction equation
Br[CH2:2][C:3]1[CH2:4][O:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH3:14])=[CH:8][CH:7]=2.C1(=O)[NH:19]C(=O)C2=CC=CC=C12.[K].O.NN.C1(=O)NC(=O)C2=CC=CC=C12>CN(C)C=O.ClCCl.C1COCC1>[CH3:14][O:13][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[O:5][CH2:4][C:3]([CH2:2][NH2:19])=[CH:12]2

Participants

8

Reactant 4

HCID 6809PhthalimideHCID 24654Hydrazine hydrate (1:1)HCID 14971319HCID 14971319, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 15391783HCID 15391783, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.17 g (4.59 mmol) of the brominated compound obtained in Step A are dissolved in 10 ml of anhydrous N,N-dimethylformamide; 1.275 g (6.9 mmol) of potassium phthalimide are then added to the medium. After 10 hours of stirring under argon, the solvent is evaporated in vacuo. The residue obtained is taken up in dichloromethane; the organic phase is then washed with water. After drying over magnesium sulphate, the solvent is evaporated in vacuo. Chromatography on a silica column (eluant: AcOEt/PE: 15/85) allows access to the corresponding phthalimide in the form of a white solid. Melting point: 141 ° C. 0.72 g (14.35 mmol) of hydrazine monohydrate is added to a solution of 1.15 g (3.58 mmol) of that phthalimide in 20 ml of THF; the mixture is then heated at reflux for 4 hours. After cooling the mixture and filtering off the solid, the filtrate is concentrated in vacuo to result in the pure title amine in the form of a yellow solid.

Workup

  1. customthe solvent is evaporated in vacuo
  2. customThe residue obtained
  3. washthe organic phase is then washed with water
  4. dry with materialAfter drying over magnesium sulphate
  5. customthe solvent is evaporated in vacuo
  6. temperaturethe mixture is then heated
  7. temperatureat reflux for 4 hours
  8. temperatureAfter cooling the mixture
  9. filtrationfiltering off the solid
  10. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-415bedbbf2a84971bf631a8d0f3b8b49
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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