Water → 1H-Pyrrole-2-carboxylic acid, 4-nitro-1-propyl-, ethyl ester

HRID 23156

Reaction equation

HRID 23156 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)=[O:5])[CH3:2].[CH3:14][CH2:15][O-].[Na+].[CH3:18]I.O>CCO.C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:18][CH2:15][CH3:14])[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 242169Ethyl 4-Nitropyrrole-2-carboxylateHCID 2723922Sodium ethoxide

Product 1

HCID 9040721H-Pyrrole-2-carboxylic acid, 4-nitro-1-propyl-, ethyl esterYield 77%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

4-Nitro-1H-pyrrole-2-carboxylic acid ethyl ester (5 g) was dissolved in 50 ml of dry EtOH, 50 ml of 1M sodium ethylate was added followed with 10 ml of CH3I. The reaction mixture was heated at 80° C. for 4 hours, cooled down to room temperature and distributed between water and chloroform. The organic phase was washed with water, dried with sodium sulfate and evaporated. The residue was recrystallized from hexane to yield 4.72 g (77%) of 1-propyl-4-nitro-1H-pyrrole-2-carboxylic acid ethyl ester 232. H1-NMR (DMSO-d6): 0.79 (t, 3H, CH3), 1.25 (t, 3H, CH3), 1.68 (m, 2H, CH2), 4.17-4.28 (m, 4H, 2CH2), 7.23 and 8.24 (d, 1H, pyrrole)

Workup

  1. temperaturecooled down to room temperature
  2. washThe organic phase was washed with water
  3. dry with materialdried with sodium sulfate
  4. customevaporated
  5. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-fd07c35c22c94de7a7c4d8b98aa27f07
Source dataset
uspto-grants-2005_02
Patent number
US06849713B2

Linked notes

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