Dichloromethane → HCID 616908, compound

HRID 1733625Notes

Reaction equation

HRID 1733625 reaction equation
CS[C:3]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19](=O)[C:18]3=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]3[C:16]2=[O:25])=[CH:11][CH:10]=1)([CH3:8])[C:4]([O:6][CH3:7])=[O:5].C(Cl)Cl>C(O)(=O)C.[Zn].S([O-])([O-])(=O)=O.[Cu+2]>[O:25]=[C:16]1[C:17]2[C:18](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][N:15]1[C:12]1[CH:13]=[CH:14][C:9]([CH:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5])=[CH:10][CH:11]=1

Participants

6

Reactant 2

HCID 6344DichloromethaneHCID 12917663HCID 12917663, compound

Product 1

HCID 616908HCID 616908, compoundYield 83.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24462Copper SulfateCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl α-methylthio-α-(p-phthalimidophenyl)propionate (355 mg), 600 mg of zinc powder and 32 mg of anhydrous copper sulfate were heated under reflux for 5 hours in 3 ml of acetic acid. Methylene chloride (30 ml) was added, and the insoluble matter was separated by filtration and washed with 20 ml of methylene chloride. The filtrate and the washing were combined, washed twice with 10 ml of water, and dried over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure. The residue was chromatographed on a silica gel column using methylene chloride as an eluent to afford 245 mg of methyl α-[p-(1-oxo-2-isoindolinyl)phenyl]propionate as colorless crystals in a yield of 83%.

Workup

  1. customthe insoluble matter was separated by filtration
  2. washwashed with 20 ml of methylene chloride
  3. washwashed twice with 10 ml of water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated off under reduced pressure
  6. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-f8142d0db78149d0bc1217f97176c258
Source dataset
uspto-grants-1980_12
Patent number
US04242519

Reaction notes

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