Triethylamine → HCID 15591048, compound

HRID 255640Notes

Reaction equation

HRID 255640 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([N:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)=[CH:15][C:14](=[O:26])[C:10]([C:11]([OH:13])=[O:12])=[CH:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:34]([O:40][CH2:41][CH2:42]I)(=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]([C:17]3[CH:18]=[CH:19][C:20]([N:23]([CH3:24])[CH3:25])=[CH:21][CH:22]=3)=[CH:15][C:14](=[O:26])[C:10]([C:11]([O:13][CH:41]([O:40][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])[CH3:42])=[O:12])=[CH:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 129278712-Iodoethyl 2,2-dimethylpropanoateHCID 15591062HCID 15591062, compound

Product 1

HCID 15591048HCID 15591048, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 10 ml of chloroform was dissolved 1 g of 1-(4-fluorophenyl)-6-(4-dimethylaminophenyl)-4-oxo-1,4-dihydronicotinic acid, and to the resulting solution were then added 0.32 g of triethylamine and 0.76 g of pivaloyloxyethyl iodide at room temperature, after which the resulting mixture was subjected to reaction at the same temperature for 2 hours. After completion of the reaction, the reaction mixture was washed successively with 20 ml of a 0.1N aqueous sodium hydroxide solution and 20 ml of water and dried with anhydrous magnesium sulfate. Then, the solvent was removed by distillation under reduced pressure, and to the residue was added 20 ml of a diethyl ether/n-hexane (1:1 by volume) mixed solvent, after which insolubles were removed by filtration to obtain 0.6 g of 1-pivaloyloxyethyl 1-(4-fluorophenyl)-6-(4-dimethylaminophenyl)-4-oxo-1,4-dihydronicotinate having a melting point of 117°-120° C.

Workup

  1. customafter which the resulting mixture was subjected to reaction at the same temperature for 2 hours
  2. customAfter completion of the reaction
  3. washthe reaction mixture was washed successively with 20 ml of a 0.1N aqueous sodium hydroxide solution and 20 ml of water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThen, the solvent was removed by distillation under reduced pressure
  6. additionto the residue was added 20 ml of a diethyl ether/n-hexane (1:1 by volume)
  7. additionmixed solvent
  8. customafter which insolubles were removed by filtration

Sources & evidence

ORD record
ord-0b67e7336ed1451d9432075e9e004e24
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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