Acetic Acid → HCID 20183833, compound

HRID 255658Notes

Reaction equation

HRID 255658 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:11]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([N:27]([CH3:29])[CH3:28])=[CH:23][CH:22]=3)=[CH:19][C:18](=[O:30])[C:13]([C:14]([O:16]C)=[O:15])=[CH:12]2)[CH:7]=[CH:8][C:9]=1[F:10])([O-])=O.O.C(Cl)(Cl)Cl.C(O)(=O)C>CN(C)C=O.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([N:11]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([N:27]([CH3:28])[CH3:29])=[CH:23][CH:22]=3)=[CH:19][C:18](=[O:30])[C:13]([C:14]([OH:16])=[O:15])=[CH:12]2)[CH:7]=[CH:8][C:9]=1[F:10]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 6212ChloroformHCID 14010730HCID 14010730, compound

Product 1

HCID 20183833HCID 20183833, compoundYield 18.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

In 12 ml of N,N-dimethylformamide was dissolved 0.6 g of methyl 1-(3-nitro-4-fluorophenyl)-6-(4-dimethylaminophenyl)-4-oxo-1,4-dihydronicotinate and to this solution was added 0.2 g of 5% by weight palladium carbon, and the above ester was hydrogenated under atmospheric pressure for 2 hours. Then, the catalyst was removed by filtration and the solvent was removed by distillation under reduced pressure. The resulting residue was dissolved in a mixture consisting of 2 ml of ethanol and 2 ml of a 1N aqueous sodium hydroxide solution, and the solution was subjected to reaction at room temperature for one hour. This reaction mixture was mixed with 10 ml of water and 10 ml of chloroform, and the mixture was adjusted to a pH of 5.5 with acetic acid. The organic layer was separated, washed successively with 10 ml of water and 10 ml of a saturated aqueous solution of sodium chloride, and dried with anhydrous magnesium sulfate. Then 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/ethanol (100:1 by volume) mixture) to obtain 0.1 g of 1-(3-amino-4-fluorophenyl)-6-(4-dimethylaminophenyl)-4-oxo-1,4-dihydronicotinic acid having a melting point of 198°-201° C.

Workup

  1. customThen, the catalyst was removed by filtration
  2. customthe solvent was removed by distillation under reduced pressure
  3. dissolutionThe resulting residue was dissolved in a mixture
  4. customthe solution was subjected to reaction at room temperature for one hour
  5. customThe organic layer was separated
  6. washwashed successively with 10 ml of water and 10 ml of a saturated aqueous solution of sodium chloride
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customThen the solvent was removed by distillation under reduced pressure
  9. customthe residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform/ethanol (100:1 by volume) mixture)

Sources & evidence

ORD record
ord-29bc601884c84347bb0e395afd4e56df
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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