Hydrazine hydrate (1:1) → Methyl 4-(2-aminoethoxy)benzoate

HRID 1762170Notes

Reaction equation

HRID 1762170 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:24]=[CH:23][C:8]([O:9][CH2:10][CH2:11][N:12]2C(=O)C3=CC=CC=C3C2=O)=[CH:7][CH:6]=1)=[O:4].O.NN>CO>[NH2:12][CH2:11][CH2:10][O:9][C:8]1[CH:23]=[CH:24][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 7679064Methyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)benzoate2×

Product 1

HCID 14097616Methyl 4-(2-aminoethoxy)benzoateYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[2-(4-Methoxycarbonylphenoxy)ethyl]phthalimide (158.86 g) prepared in accordance with (1) and 73.33 g of hydrazine hydrate were dissolved in 1.5 liters of methanol and the solution was refluxed for 1 hour. The precipitate was removed by filtration and the filtrate was concentrated in vacuo. The residue was extracted with chloroform and washed with saturated sodium chloride solution twice. The organic solvent layer was dried with anhydrous magnesium sulphate and concentrated in vacuo. n-Hexane was added to the residue to make it crystallised followed by filtration to give 85.74 g of crystals (yield: 90%). M.p. 53°-55.5° C.

Workup

  1. temperaturethe solution was refluxed for 1 hour
  2. customThe precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. extractionThe residue was extracted with chloroform
  5. washwashed with saturated sodium chloride solution twice
  6. dry with materialThe organic solvent layer was dried with anhydrous magnesium sulphate
  7. concentrationconcentrated in vacuo
  8. additionn-Hexane was added to the residue
  9. customcrystallised
  10. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-b76b4222286a48c5b15d1632fef6004d
Source dataset
uspto-grants-1989_05
Patent number
US04831055

Reaction notes

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