Water → Ethyl 1-isopentyl-4-nitro-1H-pyrrole-2-carboxylate

HRID 23146

Reaction equation

HRID 23146 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].[O-]CC.[Na+].Br[CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22].O>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 78911-Bromo-3-methylbutaneHCID 242169Ethyl 4-Nitropyrrole-2-carboxylateHCID 2723922Sodium ethoxide

Product 1

HCID 67183320Ethyl 1-isopentyl-4-nitro-1H-pyrrole-2-carboxylateYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4-Nitro-1H-pyrrole-2-carboxylic acid ethyl ester (3.69 g, 20.04 mmol) was dissolved in 100 ml of hot anhydrous ethanol and the solution was cooled to room temperature. 30 ml of sodium ethoxide (about 1M) in ethanol was added. The reaction mixture was stirred at room temperature for 20 min and 1-bromo-3-methylbutane (8 ml) was added. The mixture was stirred at reflux for 6 h and cooled to room temperature and then poured into water. The pale yellow precipitates were collected by filtration, washed with water, and dried to give the product (1.48 g, 29%).

Workup

  1. stirringThe mixture was stirred
  2. temperatureat reflux for 6 h
  3. temperaturecooled to room temperature
  4. customThe pale yellow precipitates
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-69759c971e2e427683be49f0c87c3811
Source dataset
uspto-grants-2005_02
Patent number
US06849713B2

Linked notes

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