Hydrogen Bromide → HCID 15591055, compound

HRID 255646Notes

Reaction equation

HRID 255646 reaction equation
Br.[F:2][C:3]1[CH:8]=[C:7]([O:9]C)[CH:6]=[CH:5][C:4]=1[N:11]1[C:19]([C:20]2[CH:25]=[CH:24][C:23]([N:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=2)=[CH:18][C:17](=[O:29])[C:13]([C:14]([OH:16])=[O:15])=[CH:12]1.[OH-].[Na+]>O>[F:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[N:11]1[C:19]([C:20]2[CH:21]=[CH:22][C:23]([N:26]([CH3:27])[CH3:28])=[CH:24][CH:25]=2)=[CH:18][C:17](=[O:29])[C:13]([C:14]([OH:16])=[O:15])=[CH:12]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 15591053HCID 15591053, compound

Product 1

HCID 15591055HCID 15591055, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 10 ml of 47% by weight hydrobromic acid was suspended 0.3 g of 1-(2-fluoro-4-methoxyphenyl)-6-(4-dimethylaminophenyl)-4-oxo-1,4-dihydronicotinic acid, and the suspension was refluxed for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and diluted with 10 ml of water. The resulting solution was then adjusted to a pH of 12 with 20% by weight aqueous sodium hydroxide solution and washed with 20 ml of chloroform. The aqueous layer was adjusted to a pH of 6.0 with acetic acid, and the precipitated crystals were collected by filtration, washed with 10 ml of water, and dried to obtain 0.17 g of 1-(2-fluoro-4-hydroxyphenyl)-6-(4-dimethylaminophenyl)-4-oxo-1,4-dihydronicotinic acid having a melting point of 250° C. or more.

Workup

  1. temperaturethe suspension was refluxed for 2 hours
  2. customAfter completion of the reaction
  3. washwashed with 20 ml of chloroform
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with 10 ml of water
  6. customdried

Sources & evidence

ORD record
ord-93ed06ac3a1f46718dec466af2634c2e
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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