2-Bromopropionic acid → 2-(4-Bromo-5-cyano-2-oxopyridin-1(2H)-yl)propanoic acid

HRID 56721Notes

Reaction equation

HRID 56721 reaction equation
[Br:1][C:2]1[C:3]([C:9]#[N:10])=[CH:4][NH:5][C:6](=[O:8])[CH:7]=1.Br[CH:12]([CH3:16])[C:13]([OH:15])=[O:14]>>[Br:1][C:2]1[C:3]([C:9]#[N:10])=[CH:4][N:5]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])[C:6](=[O:8])[CH:7]=1

Participants

3

Reactant 2

HCID 117292-Bromopropionic acidHCID 1176057064-Bromo-6-hydroxynicotinonitrile

Product 1

HCID 1176226522-(4-Bromo-5-cyano-2-oxopyridin-1(2H)-yl)propanoic acid

Procedure

1.0 g (purity 77%, 3.87 mmol) of 4-bromo-6-oxo-1,6-dihydropyridin-3-carbonitrile and 1.5 eq. of 2-bromopropanoic acid (racemate) were reacted according to General Method 4A at 35-45° C. After aqueous work-up, the crude product was triturated with cyclohexane/dichloromethane, and the solid was filtered off and dried under high vacuum. Yield: 648 mg (purity 66%, 41% of theory)

Workup

  1. customaccording to General Method 4A at 35-45° C
  2. customAfter aqueous work-up, the crude product was triturated with cyclohexane/dichloromethane
  3. filtrationthe solid was filtered off
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-b3bf245061af43ca9a8b7083a33dba77
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

Loading…