Pyridine-4-carbonyl chloride → HCID 10149810, compound

HRID 2182815Notes

Reaction equation

HRID 2182815 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:11]([CH3:15])[CH:12]=[CH:13][CH:14]=2)=[O:9])=[CH:4][CH:3]=1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:11]([CH3:15])[CH:12]=[C:13]([C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[O:23])[CH:14]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 417436Pyridine-4-carbonyl chlorideHCID 1116388(4-chlorophenyl)(1-methyl-1H-pyrrol-2-yl)methanoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 10149810HCID 10149810, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 17.5 g (0.08 mole) of (4-chlorophenyl)(1-methyl-1H-pyrrol-2-yl)methanone, 14.4 g (0.088 mole) of isonicotinoyl chloride and 26.6 g of aluminum chloride (0.2 mole) in 280 mL of DCE was heated under reflux for 16 h. After cooling, the mixture was partitioned between CH2Cl2 and dilute NaOH solution. The organic layer was dried and the solvent was evaporated in vacuo. The residue was triturated with ether. The resulting solid was recrystallized from 2-PrOH to give 7 g (27%) of the title compound, mp 174-175° C. ES-MS m/z=325 (M++H). 1H NMR (300 MHz, CDCl3) δ 4.1 (s, 3H); 7.1 (s, 1H); 7.3(dd, 2H); 7.42 (dd, 2H); 7.45 (s, 1H); 7.8 (dd, 2H); 8.8 (dd, 2H). Anal calc'd for: C18H13ClN2O2: C, 66.57; H, 4.03; N, 8.63. Found: C, 66.34; H, 3.94; N, 8.53.

Workup

  1. temperatureunder reflux for 16 h
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between CH2Cl2 and dilute NaOH solution
  4. customThe organic layer was dried
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was triturated with ether
  7. customThe resulting solid was recrystallized from 2-PrOH

Sources & evidence

ORD record
ord-5a3277f175fb41649eaadafccc6cb043
Source dataset
uspto-grants-2005_05
Patent number
US06897319B2

Reaction notes

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