Isoindoline → HCID 70616184, compound

HRID 1764110Notes

Reaction equation

HRID 1764110 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([CH:7]=[CH:8][CH2:9][Cl:10])=[CH:5][CH:4]=1.[CH2:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][NH:14]1>C(O)C>[ClH:10].[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([CH:7]=[CH:8][CH2:9][N:14]2[CH2:15][C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:13]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 422478IsoindolineHCID 54508890HCID 54508890, compound

Product 1

HCID 70616184HCID 70616184, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.45 gram of p-methoxycinnamyl chloride and 0.62 gram of isoindoline in 20 milliliters of ethanol is stirred overnight at room temperature. After completion of the reaction, the reaction mixture is concentrated. Chloroform is then added to the residue, and the insolubles are filtered off. The subsequent operations are carried out as in Example 13 to obtain 0.17 gram (yield 37.7%) of N-(p-methoxycinnamyl)-isoindoline hydrochloride as crystals having a melting point of 201°-202° C. (decomposition).

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture is concentrated
  3. additionChloroform is then added to the residue
  4. filtrationthe insolubles are filtered off

Sources & evidence

ORD record
ord-405f7fe9a4ed417baaa403ab0a932058
Source dataset
uspto-grants-1978_09
Patent number
US04115398

Reaction notes

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