Water → HCID 54145680, compound

HRID 1764116Notes

Reaction equation

HRID 1764116 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.C(OC([O:15][C:16]1[CH:25]=[CH:24][C:19]([CH:20]=[CH:21][CH2:22]Cl)=[CH:18][C:17]=1[O:26][CH3:27])=O)C.O>C1C=CC=CC=1.[OH-].[K+].CO>[OH:15][C:16]1[CH:25]=[CH:24][C:19]([CH:20]=[CH:21][CH2:22][N:2]2[CH2:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:1]2)=[CH:18][C:17]=1[O:26][CH3:27]

Participants

7

Reactant 3

HCID 962WaterHCID 422478IsoindolineHCID 54262883HCID 54262883, compound

Product 1

HCID 54145680HCID 54145680, compoundYield 71.7%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

The process for preparing this compound will be described below, along with its physical properties. A solution of 5.6 grams of isoindoline in 50 milliliters of benzene is added dropwise to a solution of 4.7 grams of 4-ethoxycarbonyloxy-3-methoxy-cinnamyl chloride in 30 milliliters of benzene, after which the mixture is stirred for 1 hour at room temperature and then for 2 hours at 60° C. After completion of the reaction, water is added to the reaction mixture and extracted with benzene followed by distilling the solvent off to obtain an oily product, which is dissolved in a solution of 0.95 gram of potassium hydroxide in 50 milliliters of methanol and stirred for 30 minutes at room temperature. The reaction solution is then concentrated to dryness, and a 5% aqueous sodium hydroxide solution is added to the residue to precipitate crystals, which are filtered off. After adding an excess of ammonium chloride to the mother liquor, it is extracted with chloroform. The oily product obtained after distilling off the chloroform is transformed to a maleic acid salt by operating as in Example 15, which then is recrystallized from methanol to obtain 3.5 grams (yield 56.8%) of N-(4-hydroxy-3-methoxycinnamyl)-isoindoline.maleic acid salt as crystals having a melting point of 162°-164° C. (decomposition).

Workup

  1. customThe process for preparing this compound
  2. waitfor 2 hours at 60° C
  3. additionis added to the reaction mixture
  4. extractionextracted with benzene
  5. distillationby distilling the solvent off
  6. customto obtain an oily product, which
  7. stirringstirred for 30 minutes at room temperature
  8. concentrationThe reaction solution is then concentrated to dryness
  9. additiona 5% aqueous sodium hydroxide solution is added to the residue
  10. customto precipitate crystals, which
  11. filtrationare filtered off
  12. additionAfter adding an excess of ammonium chloride to the mother liquor, it
  13. extractionis extracted with chloroform
  14. customThe oily product obtained
  15. distillationafter distilling off the chloroform
  16. customthen is recrystallized from methanol

Sources & evidence

ORD record
ord-c51c034495df429fa10a8843f947f129
Source dataset
uspto-grants-1978_09
Patent number
US04115398

Reaction notes

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