Oxalyl chloride → HCID 58961588, compound

HRID 916944Notes

Reaction equation

HRID 916944 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:14][C:13](=O)[C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][C:10]=1[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1.C(Cl)(=O)C([Cl:30])=O>ClCCl>[Cl:30][C:13]1[C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][C:10]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[N:14]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 69416016HCID 69416016, compound

Product 1

HCID 58961588HCID 58961588, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate (0.90 g, 2.2 mmol) from Example 51, Step A in dichloromethane (5 mL) was added oxalyl chloride (1.0 mL, 11.4 mmol) and the reaction was heated at 50° C. for 24 h. The reaction was concentrated in vacuo and the residue was dissolved in methylene chloride and washed with aq. sodium bicarbonate. The organic layer was washed with a portion of brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluted with 5 to 10% ethyl acetate in hexanes to yield methyl 2-chloro-6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carboxylate.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washwashed with aq. sodium bicarbonate
  4. washThe organic layer was washed with a portion of brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluted with 5 to 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-5934df9590614036a08facdfeeb5c549
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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