Acetic Acid → HCID 58243740, compound

HRID 389108Notes

Reaction equation

HRID 389108 reaction equation
Cl.[Sn].[CH3:3][O:4][C:5]1[CH:25]=[CH:24][C:8]([CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:20]([OH:22])=[O:21])[CH:16]=3)[C:11]2=O)=[CH:7][CH:6]=1.[C:26](O)(=O)C>>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:20]([O:22][CH3:26])=[O:21])[CH:16]=3)[CH2:11]2)=[CH:24][CH:25]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 748433HCID 748433, compoundHCID 5352426Tin atom2×

Product 1

HCID 58243740HCID 58243740, compound

Procedure

Concentrated hydrochloric acid (30 ml) and a tin powder (3.2 g) were added to a suspension of 2-(4-methoxybenzyl)-1,3-dioxoisoindoline-5-carboxylic acid (3.13 g) in acetic acid (30 ml), followed by stirring at room temperature for 12 hours, and a tin powder (1.2 g) was further added thereto, followed by stirring at room temperature for one day. An insoluble substance was filtered with celite, water was added to the filtrate, followed by extraction with ethyl acetate, the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The resulting residue was made into a DMF (50 ml) solution, potassium carbonate (7.0 g) and iodomethane (6.3 ml) were added thereto, followed by stirring at room temperature for 4.5 days. The reaction solution was concentrated and ethyl acetate was added to the residue, followed by washing with water and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 95:5) to obtain methyl 2-(4-methoxybenzyl)-3-oxoisoindoline-5-carboxylate (910 mg) as a colorless solid.

Workup

  1. stirringby stirring at room temperature for one day
  2. filtrationAn insoluble substance was filtered with celite, water
  3. additionwas added to the filtrate
  4. extractionfollowed by extraction with ethyl acetate
  5. washthe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. additionwere added
  9. stirringby stirring at room temperature for 4.5 days
  10. concentrationThe reaction solution was concentrated
  11. additionethyl acetate was added to the residue
  12. washby washing with water and saturated brine
  13. dry with materialAfter drying over anhydrous magnesium sulfate
  14. customthe solvent was evaporated
  15. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 95:5)

Sources & evidence

ORD record
ord-a6f9cf485fd14bf49743626b6a47ed52
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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