Sodium Hydroxide → HCID 14075285, compound

HRID 2107898Notes

Reaction equation

HRID 2107898 reaction equation
[CH3:1][N:2]1[C:10]([CH3:11])=[CH:9][C:8](=[O:12])[C:4]([C:5]([OH:7])=[O:6])=[C:3]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+].BrBr.[Br:23]C1C(=O)C(Br)=C(C)N(C)C=1C1C=CC=CC=1>CO>[Br:23][C:9]1[C:8](=[O:12])[C:4]([C:5]([OH:7])=[O:6])=[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:2]([CH3:1])[C:10]=1[CH3:11]

Participants

6

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 24408BromineHCID 14075272HCID 14075272, compoundHCID 22159935HCID 22159935, compound

Product 1

HCID 14075285HCID 14075285, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

6.0 gms of 1,6-dimethyl-2-phenyl-4-oxonicotinic acid is suspended in 200 mls of methanol. 1.0 gms of sodium hydroxide is added. As soon as the acid dissolves a solution of 5.52 gms of Br2 in 50 mls of methanol is slowly added with stirring. The pH of the reaction mixture is maintained at 8-9 by the addition of extra sodium hydroxide as required. A precipitate of 3,5-dibromo-1,6-dimethyl-2-phenyl-pyrid-4-one forms. This material is collected by filtration and discarded. Acidification of the clear filtrate yields 3.4 gms of 5-bromo-1,6-dimethyl-2-phenyl-4-oxonicotinic acid as a white solid. mp=252°-3° (acetonitrile).

Workup

  1. additionis slowly added
  2. filtrationThis material is collected by filtration

Sources & evidence

ORD record
ord-2c384001e2d54070b0dd8506fa4d7c6c
Source dataset
uspto-grants-1990_06
Patent number
US04936904

Reaction notes

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