Isoindoline → HCID 54255057, compound

HRID 1764112Notes

Reaction equation

HRID 1764112 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.C(OC([O:15][C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[CH:18]=[CH:19][CH2:20]Cl)=O)C>CO>[OH:15][C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[CH:18]=[CH:19][CH2:20][N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1

Participants

4

Reactant 2

HCID 422478IsoindolineHCID 70616038HCID 70616038, compound

Product 1

HCID 54255057HCID 54255057, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The process for the preparation of this compound and its physical properties will be given below. A solution of 5.8 grams of isoindoline in 20 milliliters of methanol is added dropwise to a solution of 3.3 grams of o-ethoxycarbonyloxycinnamyl chloride in 30 milliliters of methanol, and the resulting mixture is stirred for 1 hour at room temperature. After completion of the reaction, the methanol is distilled off, and the residue is extracted with chloroform. The chloroform layer is then purified by silica gel column chromatography and recrystallized from ethanol to obtain 1.2 grams (yield 35%) of N-(o-hydroxycinnamyl)-isoindoline as crystals having a melting point of 161°-163° C. (decomposition).

Workup

  1. customThe process for the preparation of this compound and its physical properties
  2. customAfter completion of the reaction
  3. distillationthe methanol is distilled off
  4. extractionthe residue is extracted with chloroform
  5. customThe chloroform layer is then purified by silica gel column chromatography
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f3474410709b44e8abe3b48ad1173d69
Source dataset
uspto-grants-1978_09
Patent number
US04115398

Reaction notes

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