Ethanol → HCID 19605320, compound

HRID 1603633Notes

Reaction equation

HRID 1603633 reaction equation
COC1C=CC(CN2C(=O)[CH:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]3([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])C2=O)=CC=1.O.[NH2:28]N.[CH2:30]([OH:32])C>>[CH3:30][O:32][C:15]1[CH:14]=[CH:11][C:10]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH2:28])=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 67586558N-(4-methoxybenzyl)-1-hexyl phthalimide

Product 1

HCID 19605320HCID 19605320, compound

Procedure

N-(4-methoxybenzyl)-1-hexyl phthalimide (19.9 g, 60 mmol) was dissolved in ethanol (300 ml) and hydrazine monohydrate (8.9 g, 0.11 mol) was added. The mixture was refluxed for 3 hours, filtered, the residue washed with ethanol and the filtrate evaporated. The residue was taken up in diethyl ether, filtered and the residue washed well with ether. Evaporation of the filtrate gave a yellow oil which was purified by distillation to give a clear oil bp 108-110° C., 0.02 mbar.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. filtrationfiltered
  3. washthe residue washed with ethanol
  4. customthe filtrate evaporated
  5. filtrationfiltered
  6. washthe residue washed well with ether
  7. customEvaporation of the filtrate
  8. customgave a yellow oil which
  9. distillationwas purified by distillation

Sources & evidence

ORD record
ord-c99198d203944020a6a6d772a86eb342
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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