Methanol → HCID 69418079, compound

HRID 916923Notes

Reaction equation

HRID 916923 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=[O:14])[C:11]([C:15]([OH:17])=[O:16])=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[CH3:24]O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:13][C:12](=[O:14])[C:11]([C:15]([O:17][CH3:24])=[O:16])=[CH:10][C:9]=2[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 69415322HCID 69415322, compound

Product 1

HCID 69418079HCID 69418079, compound

Procedure

Into a suspension of 6-(4-chlorophenyl)-5-(phenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (5.0 g, 15.3 mmol) from Step C in methanol (400 mL) was bubbled HCl gas until the resulting solution was saturated. The mixture was stirred at rt for 20 h, then heated at 60° C. for 8 h, and again at rt for 16 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 product. The crude product was purified by flash column chromatography on silica gel eluted with 100% methylene chloride, then a gradient of 1 to 4% methanol in methylene chloride to afford the desired title compound. HPLC/MS: 340 (M+1); Rt=3.0 min;

Workup

  1. customwas bubbled HCl gas until the resulting solution
  2. temperatureheated at 60° C. for 8 h
  3. waitagain at rt for 16 h
  4. concentrationThe reaction was concentrated in vacuo
  5. extractionextracted twice with methylene chloride
  6. washThe organic layers were washed with a portion of brine
  7. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give the crude product
  10. customThe crude product was purified by flash column chromatography on silica gel
  11. washeluted with 100% methylene chloride

Sources & evidence

ORD record
ord-a2406682252040bc8aea6a1271275ee8
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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