Methanol → HCID 117925890, compound

HRID 1054209Notes

Reaction equation

HRID 1054209 reaction equation
N1C=CC=C([C:7]([O:9][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=O)C=1.[Li].[CH3:19][OH:20]>Cl>[N:12]1[CH:13]=[CH:14][CH:15]=[C:16]([C:19]([C:16]2[C:11]([C:10]([O:9][CH3:7])=[O:17])=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:20])[CH:11]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 131736337HCID 131736337, compound

Product 1

HCID 117925890HCID 117925890, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2.5 g of crude lithium 3-picolinoylpicolinate 16 was dissolved in 40 mL of 1.25 N HCl in methanol and heated in a sealed tube at 85° C. for 2 h. After cooling, the excess solvent and reagent were removed under reduced pressure and the crude material was partitioned between 20 mL of ethyl acetate and 20 mL of saturated aqueous sodium carbonate. The aqueous layer was further extracted with 2×20 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by normal-phase flash chromatography eluting with 50-100% ethyl acetate in hexane over 29 minutes. Like fractions containing product were pooled and concentrated under reduced pressure to give methyl 3-picolinoylpicolinate 7 (240 mg, 0.99 mmol), LCMS: (M+H)+, 243.

Workup

  1. temperatureAfter cooling
  2. customthe excess solvent and reagent were removed under reduced pressure
  3. customthe crude material was partitioned between 20 mL of ethyl acetate and 20 mL of saturated aqueous sodium carbonate
  4. extractionThe aqueous layer was further extracted with 2×20 mL of ethyl acetate
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was purified by normal-phase flash chromatography
  9. washeluting with 50-100% ethyl acetate in hexane over 29 minutes
  10. additionLike fractions containing product
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d63272caa2494de0b3917ececf11607b
Source dataset
uspto-grants-2016_07
Patent number
US09394299B2

Reaction notes

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