Sodium Hydroxide → Ethyl 3-amino-1H-pyrrole-2-carboxylate

HRID 1696630Notes

Reaction equation

HRID 1696630 reaction equation
Cl.[NH2:2][C:3]1[CH:7]=[CH:6][NH:5][C:4]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[OH-].[Na+]>ClCCl>[NH2:2][C:3]1[CH:7]=[CH:6][NH:5][C:4]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 164270913-Amino-2-ethoxycarbonylpyrrole hydrochloride

Product 1

HCID 2773439Ethyl 3-amino-1H-pyrrole-2-carboxylateYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-2-ethoxycarbonylpyrrole, hydrochloride (5.0 g, 26.2 mmol) is dissolved into 25 mL of dichloromethane under argon and 13.1 mL (26.2 mmol) of a 2N sodium hydroxide solution is added dropwise. The reaction mixture is stirred vigorously for 1 h and then decanted. The aqueous phase is extracted with 25 mL of dichloromethane. The organic extracts are combined, dried on magnesium sulfate, filtered and concentrated under reduced pressure. The residue is triturated in diisopropylether and concentrated to dryness. 3-Amino-2-ethoxycarbonylpyrrole (3.93 g) is obtained as an off-white powder. El: m/z 154: [M]+ m/z 126: [M]+ —C2H5 m/z 108: [M]+ —OC2H5 (base peak) m/z 80: 108 —CO.

Workup

  1. customdecanted
  2. extractionThe aqueous phase is extracted with 25 mL of dichloromethane
  3. customdried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is triturated in diisopropylether
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-edc8a6f39cfd487fa8bc584d8f1c71e0
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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