Methanol → HCID 69416016, compound

HRID 916941Notes

Reaction equation

HRID 916941 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:15])[C:12]([C:16]([OH:18])=[O:17])=[CH:11][C:10]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1.[CH3:26]O>>[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:15])[C:12]([C:16]([O:18][CH3:26])=[O:17])=[CH:11][C:10]=1[C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 69416039HCID 69416039, compound

Product 1

HCID 69416016HCID 69416016, compound

Procedure

Into a suspension of 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (3.5 g, 8.7 mmol) from Example 32, Step A in methanol (350 mL) was bubbled HCl gas until the resulting solution was saturated. The mixture was stirred at rt for 72 h. The reaction was concentrated in vacuo, made basic with saturated sodium carbonate solution, and extracted twice with methylene chloride. The organic layers were washed with a portion of brine and the combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude methyl 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate (3.8 g) which was purified by flash column chromatography on silica gel eluted with 100% methylene chloride, then a gradient of 1 to 3% methanol in methylene chloride to give methyl 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate as an off-white solid.

Workup

  1. customwas bubbled HCl gas until the resulting solution
  2. concentrationThe reaction was concentrated in vacuo
  3. extractionextracted twice with methylene chloride
  4. washThe organic layers were washed with a portion of brine
  5. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give the crude methyl 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate (3.8 g) which
  8. customwas purified by flash column chromatography on silica gel
  9. washeluted with 100% methylene chloride

Sources & evidence

ORD record
ord-1402433efcb3441184634bc06abfe699
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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