2-Nitrobenzoyl chloride → Ethyl 1,3-dimethyl-2-(2-nitrobenzoyl)-pyrrole-5-acetate

HRID 325426Notes

Reaction equation

HRID 325426 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]1[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[N+:14]([C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20])([O-:16])=[O:15].C(=O)(O)[O-].[Na+]>C1(C)C(C)=CC=CC=1>[CH3:1][N:2]1[C:3]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:5]([CH3:7])=[C:6]1[C:19](=[O:20])[C:18]1[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 118752-Nitrobenzoyl chlorideHCID 118467Ethyl 1,4-dimethyl-1H-pyrrole-2-acetateHCID 516892Sodium Bicarbonate

Product 1

HCID 53682487Ethyl 1,3-dimethyl-2-(2-nitrobenzoyl)-pyrrole-5-acetateYield 95%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 5.7 g (0.032 mole) of ethyl 1,4-dimethylpyrrole-2-acetate and 7.0 g (0.038 mole) of 2-nitrobenzoyl chloride in 130 ml xylene is heated at reflux under nitrogen for 18 hours. The mixture is stirred vigorously over a saturated sodium bicarbonate solution for 3 hours at room temperature. The xylene layer is separated from the aqueous layer, washed with brine, dried and filtered. The filtrate is concentrated in vacuo to give 9.9 g (95%) crude ethyl 1,3-dimethyl-2-(2-nitrobenzoyl)-pyrrole-5-acetate which can be used without further purification in the next step.

Workup

  1. temperatureat reflux under nitrogen for 18 hours
  2. customThe xylene layer is separated from the aqueous layer
  3. washwashed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-ee8e14c3e7c04b038417ef037edbe398
Source dataset
uspto-grants-1984_04
Patent number
US04440779

Reaction notes

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