4-Nitrobenzoyl chloride → HCID 18424318, compound

HRID 1973681Notes

Reaction equation

HRID 1973681 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][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1)([O-:16])=[O:15]>CCOCC>[CH3:1][N:2]1[C:6]([C:21](=[O:22])[C:20]2[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:25][CH:24]=2)=[C:5]([CH3:7])[CH:4]=[C:3]1[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 118467Ethyl 1,4-dimethyl-1H-pyrrole-2-acetate

Product 1

HCID 18424318HCID 18424318, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 7.24 g (0.04 mole) of ethyl 1,4-dimethylpyrrole-2-acetate and 11.1 g (0.06 mole) of p-nitrobenzoyl chloride in 30 ml of ether under argon is stirred at room temperature in the dark for two days. The precipitate is collected by filtration. Recrystallization from isopropanol gives 11.2 g (85% yield) of ethyl 1,4-dimethyl-5-(p-nitrobenzoyl)pyrrole-2-acetate as yellow crystals, m.p. 148°-149° C.

Workup

  1. filtrationThe precipitate is collected by filtration
  2. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-0c0a586bb0644e12a12b46c86a568bc3
Source dataset
uspto-grants-1976_12
Patent number
US03998844

Reaction notes

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