Hydrazine → 1-Amino-3-methoxy-1H-pyrrole-2,4-dicarboxylic acid diethyl ester

HRID 1796623Notes

Reaction equation

HRID 1796623 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([N:18]2C(=O)C3C(=CC=CC=3)C2=O)[CH:8]=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]=1[O:11][CH3:12])=[O:5])[CH3:2].NN>CCO>[CH2:1]([O:3][C:4]([C:6]1[N:7]([NH2:18])[CH:8]=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]=1[O:11][CH3:12])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 693272701-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-methoxy-1H-pyrrole-2,4-dicarboxylic acid diethyl ester

Product 1

HCID 129859111-Amino-3-methoxy-1H-pyrrole-2,4-dicarboxylic acid diethyl esterYield 74.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 393D (0.58 g, 1.58 mmol) and NH2NH2 (60 μl, 2.21 mmol) in EtOH (5 ml) was stirred at rt overnight, filtered through Celite, the filtrate was concentrated and the residue was purified by silica gel flash column chromatography to give 393E (0.30 g, 75%) (0%-5% EtOAc—CH2Cl2).

Workup

  1. filtrationfiltered through Celite
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-4f3ffa5678524a1a8aa0ce1e435ed189
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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