Acetic Acid → HCID 54243851, compound

HRID 1764109Notes

Reaction equation

HRID 1764109 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH:4]=[CH:5][CH2:6][N:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1.[CH3:20]COCC.[N+](=C)=[N-].C(O)(=O)C>C(O)C>[CH3:20][O:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH:4]=[CH:5][CH2:6][N:7]1[CH2:8][C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:15]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 9550Diazomethane2×HCID 54255057HCID 54255057, compound

Product 1

HCID 54243851HCID 54243851, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The process for the preparation of this compound and its physical properties will be given below. 236.2 milligrams of the N-(o-hydroxycinnamyl)-isoindoline of the hereinafter-given Example 24 is dissolved in 10 milliliters of ethanol. After adding an ether solution of diazomethane thereto, the resulting mixture is left standing overnight at room temperature. The excess diazomethane is then decomposed with acetic acid, the solvent is distilled off, and the residue is recrystallized from acetone as a maleic acid salt to obtain 220.2 milligrams (yield 61.2%) of N-(o-methoxycinnamyl)-isoindoline.maleic acid salt as crystals having a melting point of 147°-148° C.

Workup

  1. customThe process for the preparation of this compound and its physical properties
  2. waitthe resulting mixture is left
  3. distillationthe solvent is distilled off
  4. customthe residue is recrystallized from acetone as a maleic acid salt

Sources & evidence

ORD record
ord-299e8d9d3ffa427d960dae17469e02f7
Source dataset
uspto-grants-1978_09
Patent number
US04115398

Reaction notes

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