Isoindoline → HCID 70616527, compound

HRID 1764107Notes

Reaction equation

HRID 1764107 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[CH:4]=[CH:5][CH2:6]Cl.[CH2:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][NH:13]1>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[CH:4]=[CH:5][CH2:6][N:13]1[CH2:14][C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12]1

Participants

4

Reactant 2

HCID 422478IsoindolineHCID 53945814HCID 53945814, compound

Product 1

HCID 70616527HCID 70616527, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The process for the preparation of this compound and its physical properties will be given below. A solution of 3.46 grams of o-chlorocinnamyl chloride and 4.41 grams of isoindoline in 20 milliliters of ethanol is stirred for 12 hours at room temperature. After cmmpletion of the reaction, the solvent is distilled off. The resulting residue is then rendered alkaline by the addition of 10% sodium hydroxide and extracted with chloroform. The chloroform layer is then purified by silica gel column chromatography, and the resulting oily product is treated as in Example 1-a to obtain 2.32 grams (yield 41% of N-(o-chlorocinnamyl)-isoindoline hydrochloride as crystals having a melting point of 170°-172° C. (decomposition).

Workup

  1. customThe process for the preparation of this compound and its physical properties
  2. customAfter cmmpletion of the reaction
  3. distillationthe solvent is distilled off
  4. additionby the addition of 10% sodium hydroxide
  5. extractionextracted with chloroform
  6. customThe chloroform layer is then purified by silica gel column chromatography
  7. additionthe resulting oily product is treated as in Example 1-a

Sources & evidence

ORD record
ord-d0199f8c7b8f4fc59e8739c3a35b9268
Source dataset
uspto-grants-1978_09
Patent number
US04115398

Reaction notes

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