Hydrazine hydrate (1:1) → Methyl alpha-methylthio-alpha-(3-chloro-4-aminophenyl)propionate

HRID 1733630Notes

Reaction equation

HRID 1733630 reaction equation
[CH3:1][S:2][C:3]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2C(=O)C3=CC=CC=C3C2=O)=[C:11]([Cl:26])[CH:10]=1)([CH3:8])[C:4]([O:6][CH3:7])=[O:5].O.NN>CO>[CH3:1][S:2][C:3]([C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([Cl:26])[CH:10]=1)([CH3:8])[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 12819454Methyl alpha-methylthio-alpha-(3-chloro-4-phthalimidophenyl)propionate

Product 1

HCID 12917666Methyl alpha-methylthio-alpha-(3-chloro-4-aminophenyl)propionateYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl α-methylthio-α-(3-chloro-4-phthalimidophenyl)propionate was suspended in 7 ml of methanol, and 97 mg of hydrazine hydrate was added. The mixture was stirred at room temperature, and then heated under reflux for 1 hour. The mixture was concentrated under reduced pressure, and an aqueous solution of ammonium chloride and methylene chloride were added. The organic layer was separated, and dried over anhydrous sodium sulfate. Concentration under reduced pressure yielded 231 mg of methyl α-methylthio-α-(3-chloro-4-aminophenyl)propionate as a pale yellow oil. Yield 92%.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionan aqueous solution of ammonium chloride and methylene chloride were added
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-c19e05afcdd54fbe9788054086601665
Source dataset
uspto-grants-1980_12
Patent number
US04242519

Reaction notes

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