Hydrochloric Acid → HCID 70616039, compound

HRID 1764106Notes

Reaction equation

HRID 1764106 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.[CH2:10]([Cl:19])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.Cl>C(O)C>[ClH:19].[CH2:10]([N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 94242Benzene, (3-chloro-1-propenyl)-HCID 422478Isoindoline

Product 1

HCID 70616039HCID 70616039, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The process for preparing this compound and its physical properties will be shown below. A mixture of 1.8 grams of isoindoline, 2.5 grams of cinnamyl chloride, 4 milliliters of triethylamine and 40 milliliters of ethanol is stirred for 4 hours at room temperature. After completion of the reaction, the solvent is distilled off, after which water is added to the residue and extracted with ether. The ether layer is collected and dried followed by distilling the ether off. The so obtained oily product is converted to a hydrochloride in a customary manner and then recrystallized from methyl ethyl ketone to obtain 1.4 grams (yield 34.6%) of N-cinnamylisoindoline hydrochloride as crystals having a melting point of 180°-182° C. (decomposition).

Workup

  1. customThe process for preparing this compound and its physical properties
  2. customAfter completion of the reaction
  3. distillationthe solvent is distilled off
  4. additionafter which water is added to the residue
  5. extractionextracted with ether
  6. customThe ether layer is collected
  7. customdried
  8. distillationby distilling the ether off
  9. customThe so obtained oily product
  10. customrecrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-4786b4956d5d4a6ab07c5b66ea7bee58
Source dataset
uspto-grants-1978_09
Patent number
US04115398

Reaction notes

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