2-Chloronicotinoyl chloride → HCID 18436873, compound

HRID 456621Notes

Reaction equation

HRID 456621 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:16]2[NH:15][CH:14]=[C:13]([C:7]3[C:6]([Cl:5])=[CH:11][CH:10]=[CH:9][C:8]=3[Cl:12])[CH:17]=2)=[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 18436873HCID 18436873, compound

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 as described in Journal of Organic Chemistry, 62: 2650 (1997) (incorporated herein by reference) 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 168 mg of (2-chloro-pyridin-3-yl)-[4-(2,6-dichloro-phenyl)-1H-pyrrol-2-yl]-methanone.

Workup

  1. customprepared
  2. customat 0° C
  3. washwashed with brine, 2N NaOH, brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel column

Sources & evidence

ORD record
ord-6262f4b57f544d29b6c00469624dc9aa
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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