Dimethyl Sulfoxide → 2-Bromo-4-(4-chloro-phenyl)-nicotinic acid

HRID 1770084Notes

Reaction equation

HRID 1770084 reaction equation
[Br:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:3]=1[C:4]([O:6]C)=[O:5].CS(C)=O.[OH-].[Na+]>O>[Br:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 200952582-Bromo-4-(4-chloro-phenyl)-nicotinic acid methyl ester

Product 1

HCID 157671372-Bromo-4-(4-chloro-phenyl)-nicotinic acidYield 87.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

50.0 g (0.15 mol) of methyl 2-bromo-4-(4-chlorophenyl)nicotinate was weighed, and 300 ml of dimethylsulfoxide and 60 ml of 30% sodium hydroxide aqueous solution were added thereto and the mixture was stirred at 80° C. for 3 hours. The mixture was then poured into water and was washed with 300 ml of ethyl acetate. Thereafter, the aqueous layer was acidified with 10% HCl aqueous solution to precipitate a crystal, which was then filtrated out. The crystal thus precipitated was washed with water and isopropyl ether, and was dried to obtain 41.0 g of a white crystal of the aimed product.

Workup

  1. washwas washed with 300 ml of ethyl acetate
  2. customto precipitate a crystal, which
  3. filtrationwas then filtrated out
  4. customThe crystal thus precipitated
  5. washwas washed with water and isopropyl ether
  6. customwas dried

Sources & evidence

ORD record
ord-225596b051a94797bad6d643edfb1912
Source dataset
uspto-grants-1995_01
Patent number
US05385880

Reaction notes

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