Hydrochloric Acid → N-(p-methylcinnamyl)-isoindoline hydrochloride

HRID 1764108Notes

Reaction equation

HRID 1764108 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH2:8][Cl:9])=[CH:4][CH:3]=1.[CH2:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][NH:13]1.Cl>C(O)C>[ClH:9].[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH2:8][N:13]2[CH2:14][C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:12]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 422478IsoindolineHCID 542056751-(3-Chloroprop-1-en-1-yl)-4-methylbenzene

Product 1

HCID 70616263N-(p-methylcinnamyl)-isoindoline hydrochlorideYield 47.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The process for the preparation of this compound and its physical properties will be given below. A solution of 5 grams of p-methylcinnamyl chloride in 50 milliliters of ethanol is added dropwise to a solution of 8.93 grams of isoindoline in 50 milliliters of ethanol, following which the mixture is stirred overnight at room temperature. After completion of the reaction, the reaction mixture is concentrated followed by adding chloroform to the residue and filtering the insolubles off. Next, the solvent is distilled off, and the residue is purified by silica gel column chromatography to obtain an oily product, which is transformed into a hydrochloride in a customary manner and recrystallized from a methanol-ether mixture to obtain 4.1 grams (yield 47.8%) of N-(p-methylcinnamyl)-isoindoline hydrochloride as crystals having a melting point of 213°-214° C. (decomposition).

Workup

  1. customThe process for the preparation of this compound and its physical properties
  2. customAfter completion of the reaction
  3. concentrationthe reaction mixture is concentrated
  4. additionby adding chloroform to the residue
  5. filtrationfiltering the insolubles off
  6. distillationNext, the solvent is distilled off
  7. customthe residue is purified by silica gel column chromatography
  8. customto obtain an oily product, which
  9. customrecrystallized from a methanol-ether mixture

Sources & evidence

ORD record
ord-ec4e8d35e5ec437bbf3c041b0e29f4a9
Source dataset
uspto-grants-1978_09
Patent number
US04115398

Reaction notes

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