Isoindoline → HCID 54026972, compound

HRID 1764113Notes

Reaction equation

HRID 1764113 reaction equation
C(OC([O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[CH:10]=[CH:11][CH2:12]Cl)=O)C.[CH2:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][NH:18]1>CO>[OH:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[CH:10]=[CH:11][CH2:12][N:18]1[CH2:19][C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:17]1

Participants

4

Reactant 2

HCID 422478IsoindolineHCID 54018822HCID 54018822, compound

Product 1

HCID 54026972HCID 54026972, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The process for the preparation of this compound and its physical properties will be given below. 4.8 grams of m-ethoxycarbonyloxycinnamyl chloride and 7.15 grams of isoindoline are dissolved in 70 milliliters of methanol, and the resulting solution is stirred for 2 hours at room temperature. After completion of the reaction, the methanol is distilled off, and the residue is extracted with benzene. The resulting extract is then purified by silica gel column chromatography and recrystallized from methanol to obtain 1.2 grams (yield 23.9%) of N-(m-hydroxycinnamyl)-isoindoline as crystals having a melting point of 164.5°-165.5° C.

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 benzene
  5. extractionThe resulting extract
  6. customis then purified by silica gel column chromatography
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-78a15cfda2974782b78d15b5c90d2db7
Source dataset
uspto-grants-1978_09
Patent number
US04115398

Reaction notes

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