Pyrrole → HCID 18436869, compound

HRID 456645Notes

Reaction equation

HRID 456645 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:7]=1[C:8](Cl)=[O:9].[NH:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1>C(Cl)Cl.C(OCC)(=O)C>[Cl:5][C:6]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:7]=1[C:8]([C:19]1[NH:18][CH:22]=[CH:21][CH:20]=1)=[O:9]

Participants

6

Reactant 3

HCID 8027PyrroleHCID 117637Benzoyl chloride, 2-chloro-5-nitro-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 18436869HCID 18436869, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Aluminum chloride (2.6 g, 20 mmol) was added to a mixture of 2-chloro-5-nitro-benzoyl chloride (5 g, 20 mmol) and pyrrole (4 g, 30 mmol) in DCM (100 mL) at 0° C. The mixture was stirred at 0° C. for 30 mins. The reaction was diluted with ethyl acetate, washed with brine, water, NaHCO3, dried and concentrated. The residue was purified on a silica gel column to give 1.5 g (30%) of (2-chloro-5-nitro-phenyl)-(1H-pyrrol-2-yl)-methanone.

Workup

  1. washwashed with brine, water, NaHCO3
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-84332fdb95f5497ca76d0acb14116523
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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