Water → HCID 53775450, compound

HRID 1764115Notes

Reaction equation

HRID 1764115 reaction equation
C(OC([O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[O:17]C(OCC)=O)[CH:10]=[CH:11][CH2:12]Cl)=O)C.[CH2:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][NH:24]1.O>C1C=CC=CC=1>[OH:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[OH:17])[CH:10]=[CH:11][CH2:12][N:24]1[CH2:25][C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:23]1

Participants

5

Reactant 3

HCID 962WaterHCID 422478IsoindolineHCID 54511256HCID 54511256, compound

Product 1

HCID 53775450HCID 53775450, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

The process for preparing this compound and its physical properties will be given below. A solution of 2.6 grams of 3,4-diethoxycarbonyloxycinnamyl chloride in 10 milliliters of benzene is added dropwise with stirring to a solution of 3.8 grams of isoindoline in 20 milliliters of benzene while cooling the reaction system with ice. After completion of the dropping, the reaction is carried out for 2 hours at room temperature. On completion of the reaction, water and a large quantity of benzene are added followed by separating and collecting the benzene layer. After concentrating the benzene layer, it is left to stand under cooled conditions to precipitate crystals. When these crystals are recrystallized from a tetrahydrofuran-ether mixture, 1.1 grams (yield 52.1%) of N-(3,4-dihydroxycinnamyl)-isoindoline is obtained as crystals having a melting point of 60.5° C. (decomposition).

Workup

  1. customThe process for preparing this compound and its physical properties
  2. temperaturewhile cooling the reaction system with ice
  3. customby separating
  4. customcollecting the benzene layer
  5. concentrationAfter concentrating the benzene layer, it
  6. waitis left
  7. customto precipitate crystals
  8. customWhen these crystals are recrystallized from a tetrahydrofuran-ether mixture

Sources & evidence

ORD record
ord-f376131ca985497a989b346c47ad321a
Source dataset
uspto-grants-1978_09
Patent number
US04115398

Reaction notes

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