Hydrochloric Acid → 2-(5-Bromo-2-oxopyridin-1(2H)-yl)propanoic acid

HRID 1878702Notes

Reaction equation

HRID 1878702 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:15])[N:6]([CH:8]([CH3:14])[C:9]([O:11]CC)=[O:10])[CH:7]=1.[OH-].[Na+].Cl>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:15])[N:6]([CH:8]([CH3:14])[C:9]([OH:11])=[O:10])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58070448Ethyl 2-(5-bromo-2-oxopyridin-1(2H)-yl)propanoate

Product 1

HCID 580705082-(5-Bromo-2-oxopyridin-1(2H)-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(5-bromo-2-oxopyridin-1(2H)-yl)propanoate (5.0 g, 18 mmol) in 40 mL of 1:1 THF/MeOH are rt was added 25 mL of 1N NaOH. The reaction was stirred at rt for 5 hours and was then acidified with 2N HCl to pH˜2. The solid formed was collected and was washed with water and EtOAc to give white solid (4.2 g, 94% yield) as desired product. MS (ESI pos. ion) m/z (MH+): 245.9. Calc'd Exact Mass for C8H8BrNO3: 244.97.

Workup

  1. customare rt
  2. customThe solid formed
  3. customwas collected
  4. washwas washed with water and EtOAc

Sources & evidence

ORD record
ord-90f37a3e98a949878a398c09a46082b3
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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