Sodium Hydroxide → HCID 15582862, compound

HRID 485204Notes

Reaction equation

HRID 485204 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])=[CH:4][C:3]=1[O:19][CH:20]([C:22]([O:24]CC)=[O:23])[CH3:21].[OH-].[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])=[CH:4][C:3]=1[O:19][CH:20]([C:22]([OH:24])=[O:23])[CH3:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15582850HCID 15582850, compound

Product 1

HCID 15582862HCID 15582862, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4.7 g. of N-[4-bromo-3-(1-ethoxycarbonylethyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide, 15 ml. of methanol and 4 ml. of 40% aqueous solution of sodium hydroxide was refluxed with stirring for 1 hour and the solvent was distilled off under a reduced pressure. The residue was mixed with 0.4 g. of cyclohexane-1,2-dicarboxylic anhydride and 20 ml. of glacial acetic acid and the mixture was refluxed with stirring for 3 hours and the reaction mixture was poured into 1 liter of water to precipitate the product. The precipitate was separated by a filtration and washed with water and dried. The residue was purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate:n-hexane of 8:1) to obtain 3.8 g. of Compound No. 10 shown in Table 1.

Workup

  1. additionA mixture of 4.7 g
  2. distillationthe solvent was distilled off under a reduced pressure
  3. additionThe residue was mixed with 0.4 g
  4. temperatureof glacial acetic acid and the mixture was refluxed
  5. stirringwith stirring for 3 hours
  6. additionthe reaction mixture was poured into 1 liter of water
  7. customto precipitate the product
  8. customThe precipitate was separated by a filtration
  9. washwashed with water
  10. customdried
  11. customThe residue was purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate:n-hexane of 8:1)
  12. customto obtain 3.8 g

Sources & evidence

ORD record
ord-609ea25d37594d06a95a5437dafff54b
Source dataset
uspto-grants-1985_08
Patent number
US04536209

Reaction notes

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