Water → HCID 15591089, compound

HRID 255648Notes

Reaction equation

HRID 255648 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[CH:11]=[C:12]([C:16](=[O:18])[CH:17]=2)[C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28].O>C(OCC)(=O)C>[C:27]([O:25][C:22]1[CH:21]=[CH:20][C:19]([N:10]2[C:9]([C:6]3[CH:7]=[CH:8][C:3]([N:2]([CH3:26])[CH3:1])=[CH:4][CH:5]=3)=[CH:17][C:16](=[O:18])[C:12]([C:13]([OH:15])=[O:14])=[CH:11]2)=[CH:24][CH:23]=1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 30219833-Pyridinecarboxylic acid, 1,4-dihydro-6-(4-(dimethylamino)phenyl)-1-(4-hydroxyphenyl)-4-oxo-

Product 1

HCID 15591089HCID 15591089, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

With 1 g of 6-(4-dimethylaminophenyl)-1-(4-hydroxyphenyl)-4-oxo-1,4-dihydronicotinic acid was mixed 10 ml of acetic anhydride and the resulting mixture was subjected to reaction at 130° C. for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and introduced into 150 ml of water. After stirring the mixture for 1 hour, 150 ml of ethyl acetate was added to the mixture, and the organic layer was separated, washed with 100 ml of water and then with 50 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 to the residue was added 20 ml of diethyl ether, and the resulting mixture was filtered to obtain 0.75 g of 1-(4-acetyloxyphenyl)-6-(4-dimethylaminophenyl)-4-oxo-1,4-dihydronicotinic acid having a melting point of 128°-131° C.

Workup

  1. customthe resulting mixture was subjected to reaction at 130° C. for 2 hours
  2. customAfter completion of the reaction
  3. customthe organic layer was separated
  4. washwashed with 100 ml of water
  5. dry with materialwith 50 ml of a saturated aqueous solution of sodium chloride, and dried with anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. additionto the residue was added 20 ml of diethyl ether
  8. filtrationthe resulting mixture was filtered

Sources & evidence

ORD record
ord-40cfa446a48d45ddaddd03a557aa97c4
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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