Hydrazine hydrate (1:1) → 1-Methyl-1H-pyrrole-2-acetic acid

HRID 234614Notes

Reaction equation

HRID 234614 reaction equation
O.NN.[CH3:4][N:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH2:10][C:11]([O:13]C)=[O:12]>C(O)C>[CH3:4][N:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH2:10][C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 103992Methyl 1-methylpyrrol-2-acetate

Product 1

HCID 890951-Methyl-1H-pyrrole-2-acetic acidYield 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (65 ml) was added dropwise to a solution of methyl 1-methyl-1H-pyrrole-2-acetate (0.326 mol) in ethanol (300 ml) and the mixture was refluxed for 4 hours. The mixture was evaporated till dryness. The residue was taken up in dichloromethane and an aqueous potassium carbonate solution (10%) and extracted with dichloromethane. The organic layer was dried (MgSO4) and evaporated. The residue (48.8 g) was taken up in 1,1'-oxybisethane and the precipitate was filtered off, yielding 45.3 g (90%) of 1-methyl-1H-pyrrole-2-acetic acid, hydrazine (interm. 7).

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customThe mixture was evaporated till dryness
  3. extractionan aqueous potassium carbonate solution (10%) and extracted with dichloromethane
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated
  6. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-1606391d53524f5db959d205bbe2579e
Source dataset
uspto-grants-1997_01
Patent number
US05595988

Reaction notes

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