Methanol → HCID 14459971, compound

HRID 892835Notes

Reaction equation

HRID 892835 reaction equation
Br[CH:2](Br)[C:3]1[CH:4]=[CH:5][C:6]([C:9]([O:11][CH3:12])=[O:10])=[N:7][CH:8]=1.[C:14]([O-:17])(O)=O.[Na+].[Na+].[Cl-].[CH3:21][OH:22]>C(OC)(OC)OC.O.[N+]([O-])([O-])=O.[Ag+]>[CH3:21][O:22][CH:2]([O:17][CH3:14])[C:3]1[CH:4]=[CH:5][C:6]([C:9]([O:11][CH3:12])=[O:10])=[N:7][CH:8]=1

Participants

8

Reactant 4

HCID 887Methanol2×HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 19754543Methyl 5-(dibromomethyl)pyridine-2-carboxylate

Product 1

HCID 14459971HCID 14459971, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 9005Trimethyl orthoformateSolvent

Procedure

To a solution of methyl 5-(dibromomethyl)pyridine-2-carboxylate (927 mg, 3.00 mmol) in methanol (10 ml) and trimethyl orthoformate (2 ml) was added a solution AgNO3 (1.12 g, 6.6 mmol) in methanol (20 ml) over 15 minutes. After refluxing the reaction for 1 hour, it was cooled and poured into a solution of NaHCO3 (0.84 g, 10 mmol) in water (50 ml) containing a small amount of NaCl. The thick slurry was filtered through a 25-50 micron frit, and the filtrate concentrated to 10 ml and extracted with ethyl acetate (3×10 ml). The combined organic layers were dried (MgSO4), filtered and concentrated to give title product (550 mg, 96%).

Workup

  1. temperatureAfter refluxing
  2. customthe reaction for 1 hour
  3. temperatureit was cooled
  4. filtrationThe thick slurry was filtered through a 25-50 micron frit
  5. concentrationthe filtrate concentrated to 10 ml
  6. extractionextracted with ethyl acetate (3×10 ml)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9ed5cf0a9b55464ab97296fa4233b33a
Source dataset
uspto-grants-1992_06
Patent number
US05120754

Reaction notes

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