Acetic Acid → Ethyl 3-amino-1H-pyrrole-2-carboxylate

HRID 242839Notes

Reaction equation

HRID 242839 reaction equation
[C:1]([CH:3]=[CH:4][NH:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])C(OCC)=O)#[N:2].C(O)(=O)C>C(O)C.C([O-])C.[Na+]>[NH2:2][C:1]1[CH:3]=[CH:4][NH:5][C:6]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 573462111,3-Diethyl 2-[(2-cyanoeth-1-EN-1-YL)amino]propanedioate

Product 1

HCID 2773439Ethyl 3-amino-1H-pyrrole-2-carboxylateYield 54.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 2723922Sodium ethoxideSolvent

Procedure

Into a 1000-mL round-bottom flask was placed a solution of diethyl 2-(2-cyanovinylamino)malonate (30 g, 119.3 mmol, 1.00 equiv, 90%) in ethanol (420 mL) and sodium ethanolate (80 mL, 21%). The resulting solution was stirred for 3 days at room temperature. After the addition of acetic acid (15 ml), the resulting mixture was concentrated under vacuum, dissolved in 200 mL of dichloromethane, washed with 2×100 mL of saturated aqueous sodium bicarbonate and 1×100 mL of brine, dried over anhydrous sodium sulfate and concentrated. The residue was dried in HV to afford 10 g (49%) of ethyl 3-amino-1H-pyrrole-2-carboxylate as an orange syrup.

Workup

  1. customInto a 1000-mL round-bottom flask was placed
  2. concentrationthe resulting mixture was concentrated under vacuum
  3. dissolutiondissolved in 200 mL of dichloromethane
  4. washwashed with 2×100 mL of saturated aqueous sodium bicarbonate and 1×100 mL of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was dried in HV

Sources & evidence

ORD record
ord-3e0f8f18948443feaae0b049d89d3bf4
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…