2-Chloronicotinoyl chloride → HCID 18436872, compound

HRID 456619Notes

Reaction equation

HRID 456619 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([C:11]2[CH:15]=[CH:14][NH:13][CH:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl:16][C:17]1[N:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20]>C(Cl)Cl.C(OCC)(=O)C>[Cl:16][C:17]1[C:18]([C:19]([C:12]2[NH:13][CH:14]=[CH:15][C:11]=2[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:20])=[CH:22][CH:23]=[CH:24][N:25]=1

Participants

6

Reactant 3

HCID 27745412-Chloronicotinoyl chlorideHCID 53241103-phenyl-1H-pyrroleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18436872HCID 18436872, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Aluminum chloride (1.33 g, 10 mmol) was added to a mixture of 3-phenyl-1H-pyrrole (1.35 g, 9.4 mmol, prepared as described in Journal of Organic Chemistry, 62: 2650 (1997) (incorporated herein by reference) and 2-chloronicotinoyl chloride (1.65 g, 9.4 mmol) in DCM (15 mL) at 0° C. The mixture was stirred at 0° C. for 30 mins and at room temperature for one hour. 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 0.682 g (26%) of (2-chloro-pyridin-3-yl)-(3-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-f4d4b40ed8c845d1934b03128835c46a
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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