Hydrazine hydrate (1:1) → HCID 19790226, compound

HRID 1154178Notes

Reaction equation

HRID 1154178 reaction equation
C1(=O)[N:5]([O:6][CH2:7]/[CH:8]=[CH:9]/[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])C(=O)C2=CC=CC=C12.O.NN>C(Cl)Cl.CO>[NH2:5][O:6][CH2:7]/[CH:8]=[CH:9]/[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19790246HCID 19790246, compound

Product 1

HCID 19790226HCID 19790226, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-phthalimidooxycrotonate (20.0 g) in methylene chloride (140 ml) was added a solution of hydrazine monohydrate (5.0 g) in methanol (10 ml) with stirring, and the stirring was continued at ambient temperature for 15 minutes. The insoluble substance was collected by filtration and washed with methylene chloride. The washings and the filtrate were combined and then extracted three times with 5% hydrochloric acid. After the combined extracts were washed with diethyl ether, thereto was added methylene chloride, followed by adjusting to pH 7.5 with 28% aqueous ammonium hydroxide. The separated methylene chloride solution was washed with a saturated aqueous sodium chloride and then dried over magnesium sulfate. Removal of the solvent gave an oil of tert-butyl 4-aminooxycrotonate (11.03 g).

Workup

  1. filtrationThe insoluble substance was collected by filtration
  2. washwashed with methylene chloride
  3. extractionextracted three times with 5% hydrochloric acid
  4. washAfter the combined extracts were washed with diethyl ether
  5. additionwas added methylene chloride
  6. washThe separated methylene chloride solution was washed with a saturated aqueous sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-262cda057c1a4abeab48a3c785da64bb
Source dataset
uspto-grants-1984_12
Patent number
US04487927

Reaction notes

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