Dimethylformamide → HCID 70513486, compound

HRID 326025Notes

Reaction equation

HRID 326025 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][CH2:7][CH2:8][N:9]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:25])=[O:4].C1(=O)[NH:30]C(=O)C2=CC=CC=C12.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[NH2:30][CH2:2][C:3]([NH:5][CH2:6][CH2:7][CH2:8][N:9]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:25])=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 70513291HCID 70513291, compound

Product 1

HCID 70513486HCID 70513486, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

7.1 g of 2-(2-chloroacetamidopropyl)-4-phenyl-1(2H)-isoquinolone, 3.7 g of phthalimide and 3.7 g of potassium carbonate were added to 50 ml of dimethylformamide, and the mixture was stirred at 80° C. for 5 hours. The resulting reaction mixture was poured into water and the precipitated crystals were collected by filtration, washed with water and dried in air. The resulting crystals and 2 g of hydrazine hydrate were added to 100 ml of ethanol and the mixture was heated at reflux for 3 hours. After allowing the mixture to cool, 5 ml of concentrated hydrochloric acid was added to the resulting reaction mixture and the mixture was stirred for 5 hours. The solvent was then distilled off, and water was added to the residue, followed by thoroughly stirring. The mixture was filtered and the filtrate was rendered neutral with a 10% aqueous solution of sodium hydroxide. The precipitated was extracted with dichloromethane, and the extract was washed with water and dried. The solvent was distilled off and the resulting crystals were recrystallized from a mixture of ethyl acetate and petroleum ether to obtain 2.3 g (34% yield) of 2-(2-aminoacetamidopropyl)-4-phenyl-1(2H)-isoquinolone having a melting point of 141° C. as colorless needles.

Workup

  1. customThe resulting reaction mixture
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed with water
  4. customdried in air
  5. additionThe resulting crystals and 2 g of hydrazine hydrate were added to 100 ml of ethanol
  6. temperaturethe mixture was heated
  7. temperatureat reflux for 3 hours
  8. temperatureto cool
  9. addition5 ml of concentrated hydrochloric acid was added to the resulting reaction mixture
  10. stirringthe mixture was stirred for 5 hours
  11. distillationThe solvent was then distilled off
  12. additionwater was added to the residue
  13. stirringby thoroughly stirring
  14. filtrationThe mixture was filtered
  15. extractionThe precipitated was extracted with dichloromethane
  16. washthe extract was washed with water
  17. customdried
  18. distillationThe solvent was distilled off
  19. customthe resulting crystals were recrystallized from a mixture of ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-521f73bfdc2d4a40aba3ba759d7fdf6a
Source dataset
uspto-grants-1984_04
Patent number
US04443607

Reaction notes

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