Hydrochloric Acid → 5-(2-Acetamido-5-methylpyridin-4-yl)-2-bromo-3-furoic acid

HRID 537063Notes

Reaction equation

HRID 537063 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:15][C:14]([Br:16])=[C:13]([C:17]([O:19]CC)=[O:18])[CH:12]=2)[C:8]([CH3:22])=[CH:7][N:6]=1)(=[O:3])[CH3:2].Cl>CCO.[OH-].[Na+]>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:15][C:14]([Br:16])=[C:13]([C:17]([OH:19])=[O:18])[CH:12]=2)[C:8]([CH3:22])=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66748591Ethyl 5-(2-acetamido-5-methylpyridin-4-yl)-2-bromo-3-furoate

Product 1

HCID 667484985-(2-Acetamido-5-methylpyridin-4-yl)-2-bromo-3-furoic acidYield 54%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of ethyl 5-(2-acetamido-5-methylpyridin-4-yl)-2-bromo-3-furoate (20 g, 54.6 mmol) in EtOH (240 mL) and 1M NaOH (80 mL) was allowed to stir at rt for 2 h. The reaction mixture was acidified with concentrated HCl to pH=3-4 and then filtered. The resulting solid was washed with water and dried to give 5-(2-acetamido-5-methylpyridin-4-yl)-2-bromo-3-furoic acid (10.0 g, 43%).

Workup

  1. filtrationfiltered
  2. washThe resulting solid was washed with water
  3. customdried

Sources & evidence

ORD record
ord-befcb54a76a34e86a686e4b31fffdf6e
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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