Water → HCID 12819450, compound

HRID 1277773Notes

Reaction equation

HRID 1277773 reaction equation
CS[C:3]([C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([Cl:16])[CH:10]=1)([CH3:8])[C:4]([O:6][CH3:7])=[O:5].O.C(OCC)C>C(O)(=O)C.[Zn].S([O-])([O-])(=O)=O.[Cu+2]>[Cl:16][C:11]1[CH:10]=[C:9]([CH:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5])[CH:14]=[CH:13][C:12]=1[NH2:15]

Participants

7

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 12917666Methyl alpha-methylthio-alpha-(3-chloro-4-aminophenyl)propionate

Product 1

HCID 12819450HCID 12819450, compoundYield 95.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24462Copper SulfateCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl α-methylthio-α-(3-chloro-4-aminophenyl)propionate (380 mg) was dissolved in 4 ml of acetic acid, and an intimate mixture of 406 mg of zinc powder and 1.5 mg of anhydrous copper sulfate was added. The entire mixture was heated under reflux for 1 hour. Water (40 ml) and 15 ml of diethyl ether were added to the reaction mixture. The insoluble matter was separated by filtration, and then the organic layer was separated. Furthermore, the aqueous layer was extracted with 5 ml of diethyl ether. The organic layer and the extract were combined, washed with 15 ml of a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford 299 mg of methyl α-(3-chloro-4-aminophenyl)propionate in a yield of 95.6% as a colorless oil.

Workup

  1. additionwas added
  2. temperatureThe entire mixture was heated
  3. temperatureunder reflux for 1 hour
  4. customThe insoluble matter was separated by filtration
  5. customthe organic layer was separated
  6. extractionFurthermore, the aqueous layer was extracted with 5 ml of diethyl ether
  7. washwashed with 15 ml of a saturated aqueous solution of sodium hydrogen carbonate
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9035337a270a49b98fdece3c4dd1c968
Source dataset
uspto-grants-1981_07
Patent number
US04278802

Reaction notes

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