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

HRID 1507474Notes

Reaction equation

HRID 1507474 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+]>>[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

3

Reactant 2

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

Product 1

HCID 2773439Ethyl 3-amino-1H-pyrrole-2-carboxylateYield 90%

Procedure

A 2 l conical flask is charged, with magnetic stirring, with 50 g of 3-amino-2-ethoxycarbonylpyrrole hydrochloride and 0.204 l of 2N sodium hydroxide solution. The mixture is stirred for 15 minutes at ambient temperature (AT), and then extracted with 3×0.3 l of dichloromethane. The organic phases are combined, dried over MgSO4 and concentrated to dryness under reduced pressure. The residue is triturated with n-pentane, filtered and dried under reduced pressure to a constant weight, to give 36.4 g of 3-amino-2-ethoxycarbonylpyrrole in the form of a brown solid.

Workup

  1. extractionextracted with 3×0.3 l of dichloromethane
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe residue is triturated with n-pentane
  5. filtrationfiltered
  6. customdried under reduced pressure to a constant weight

Sources & evidence

ORD record
ord-f49106d470514714855ebe07f5d72e4b
Source dataset
uspto-grants-2015_12
Patent number
US09221817B2

Reaction notes

Loading…