2-Chloronicotinoyl chloride → HCID 18436870, compound

HRID 456623Notes

Reaction equation

HRID 456623 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[C:13]1[CH:17]=[CH:16][NH:15][CH:14]=1.[Cl:18][C:19]1[N:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22]>C(Cl)Cl.C(OCC)(=O)C>[Cl:18][C:19]1[C:20]([C:21]([C:14]2[NH:15][CH:16]=[CH:17][C:13]=2[C:7]2[C:6]([Cl:5])=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:12])=[O:22])=[CH:24][CH:25]=[CH:26][N:27]=1

Participants

6

Reactant 3

HCID 27745412-Chloronicotinoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12665445HCID 12665445, compound

Product 1

HCID 18436870HCID 18436870, compoundYield 4.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Aluminum chloride (1.4 g, 10.5 mmol) was added to a mixture of 3-(2,6-dichloro-phenyl)-1H-pyrrole (2 g, prepared according to JOC, 62, 1997, 2650) and 2-chloronicotinoyl chloride (1.8 g, 10.5 mmol) in DCM (55 mL) at 0° C. The mixture was stirred at 0° C. for 30 mins and at room temperature for 1.5 hours. The reaction was diluted with ethyl acetate and washed with brine, 2N NaOH, brine, dried and concentrated. The residue was purified on silica gel column to give 160 mg of (2-chloro-pyridin-3-yl)-[3-(2,6-dichloro-phenyl)-1H-pyrrol-2-yl]-methanone.

Workup

  1. washwashed with brine, 2N NaOH, brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified on silica gel column

Sources & evidence

ORD record
ord-0b0c8cc202774c8ca7a4ece91b99a69b
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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