Hydrogen Bromide → HCID 15591094, compound

HRID 255653Notes

Reaction equation

HRID 255653 reaction equation
Br.C1[O:10][C:9]2[CH:8]=[CH:7][C:6]([N:11]3[C:19]([C:20]4[CH:25]=[CH:24][C:23]([N:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=4)=[CH:18][C:17](=[O:29])[C:13]([C:14]([OH:16])=[O:15])=[CH:12]3)=[CH:5][C:4]=2[O:3]1.[OH-].[Na+]>O>[OH:3][C:4]1[CH:5]=[C:6]([N:11]2[C:19]([C:20]3[CH:21]=[CH:22][C:23]([N:26]([CH3:27])[CH3:28])=[CH:24][CH:25]=3)=[CH:18][C:17](=[O:29])[C:13]([C:14]([OH:16])=[O:15])=[CH:12]2)[CH:7]=[CH:8][C:9]=1[OH:10]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 15591061HCID 15591061, compound

Product 1

HCID 15591094HCID 15591094, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 10 ml of 47% by weight hydrobromic acid was suspended 0.15 g of 1-(3,4-methylenedioxyphenyl)-6-(4-dimethylaminophenyl)-4-oxo-1,4-dihydronicotinic acid, and they were refluxed for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and diluted with 10 ml of water. This solution was adjusted to a pH of 12 with a 20% weight aqueous sodium hydroxide solution, washed with 20 ml of chloroform, and again adjusted to a pH of 6.0 with acetic acid. This solution was extracted with 50 ml of chloroform, and the extract was washed with 30 ml of a saturated aqueous solution of sodium chloride and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform/methanol (15:1 by volume) mixture) to obtain 0.05 g of 1-(3,4-dihydroxyphenyl)-6-(4-dimethylaminophenyl)-4-oxo-1,4-dihydronicotinic acid having a melting point of 223°-227° C.

Workup

  1. temperaturewere refluxed for 2 hours
  2. customAfter completion of the reaction
  3. washwashed with 20 ml of chloroform
  4. extractionThis solution was extracted with 50 ml of chloroform
  5. washthe extract was washed with 30 ml of a saturated aqueous solution of sodium chloride
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform/methanol (15:1 by volume) mixture)

Sources & evidence

ORD record
ord-6c81f4e920274383b4b765974ac4438d
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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