Pyrrole → HCID 14500627, compound

HRID 1761574Notes

Reaction equation

HRID 1761574 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[NH:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([C:14]1[NH:13][CH:17]=[CH:16][CH:15]=1)=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 8027PyrroleHCID 8495Benzoyl chloride, 3-nitro-

Product 1

HCID 14500627HCID 14500627, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Alternatively, about 0.5 to 2 molar equivalents of m-nitrobenzoyl chloride (Formula ;b 7 where Z is chloro) (available from Aldrich) is added to pyrrole or an optionally substituted pyrrole (represented by Formula 8, prepared, e.g., as described in Reaction Schemes 1 and 2) dissolved in an inert organic solvent (preferably toluene) and heated, preferably to the reflux temperature of the solvent used, in an inert atmosphere (e.g., under nitrogen). The reaction takes place over a period of about 1 to 30 hours, preferably 10 to 25 hours, and most preferably about 18 hours. The 2-(3'-nitrobenzoyl)pyrrole intermediate of Formula 9 is isolated and purified in the usual manner.

Workup

  1. temperatureheated, preferably to the reflux temperature of the solvent
  2. customof about 1 to 30 hours
  3. custompreferably 10 to 25 hours, and most preferably about 18 hours

Sources & evidence

ORD record
ord-2522a8d290254e0f9601257d24d2ace6
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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