Methanol → Methyl 5-bromopyridine-3-carboxylate

HRID 235512Notes

Reaction equation

HRID 235512 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:11]O>Cl>[CH3:11][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 887075-Bromonicotinic acid

Product 1

HCID 699336Methyl 5-bromopyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-Bromo-nicotinic acid (5,00 g, 24.7 mmol) was dissolved in methanol (50 mL) and saturated with hydrochloric acid gas. The reaction mixture was allowed to stand for 2.5 days and then filtered. The filtrate was concentrated under reduced pressure and methylene chloride was added. The solution was washed with saturated sodium bicarbonate solution. The aqueous wash was back-extracted with methylene chloride (2x). The combined organic extracts were dried over magnesium sulfate and concentrated in vacuo to afford 5-bromo-nicotinic acid methyl ester (4.72 g).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure and methylene chloride
  3. additionwas added
  4. washThe solution was washed with saturated sodium bicarbonate solution
  5. washThe aqueous wash
  6. extractionwas back-extracted with methylene chloride (2x)
  7. dry with materialThe combined organic extracts were dried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2494aa346e1f495c8d2ed9d8d135ff3c
Source dataset
uspto-grants-1997_01
Patent number
US05597926

Reaction notes

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