Hydrogen Bromide → HCID 15591128, compound

HRID 255643Notes

Reaction equation

HRID 255643 reaction equation
Br.[F:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=3)=[CH:16][C:15](=[O:26])[C:11]([C:12]([OH:14])=[O:13])=[CH:10]2)=[CH:5][CH:4]=1.[OH-].[Na+]>O>[F:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)=[CH:16][C:15](=[O:26])[C:11]([C:12]([OH:14])=[O:13])=[CH:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 15591117HCID 15591117, compound

Product 1

HCID 15591128HCID 15591128, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 7 ml of 47% by weight hydrobromic acid was suspended 0.2 g of 1-(4-fluorophenyl)-6-(4-methoxyphenyl)-4-oxo-1,4-dihydronicotinic acid was suspended, and the suspension was refluxed for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with 10 ml of water, adjusted to a pH of 12 with a 20% by weight aqueous sodium hydroxide solution, and washed with 20 ml of chloroform. This aqueous solution was then adjusted to a pH of 6.0 with acetic acid and the precipitated crystals were collected by filtration, and washed with water to obtain 0.15 g of 1-(4-fluorophenyl)-6-(4-hydroxyphenyl)-4-oxo-1,4-dihydronicotinic acid having a melting point of 185°-193° C.

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 water

Sources & evidence

ORD record
ord-5e270d420c244205b4b284b426e9bceb
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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