Dimethylformamide → HCID 14010791, compound

HRID 255656Notes

Reaction equation

HRID 255656 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](=[O:30])([O-])[O-].[K+].[K+].[CH3:33][O:34][CH2:35]Cl.[CH3:37]N(C)C=O>>[CH3:1][N:2]([CH3:26])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH2:37][O:30][CH3:27])=[CH:23][CH:24]=3)[CH:11]=[C:12]([C:16](=[O:18])[CH:17]=2)[C:13]([O:15][CH2:33][O:34][CH3:35])=[O:14])=[CH:5][CH:4]=1.[CH3:1][N:2]([CH3:26])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)[CH:11]=[C:12]([C:16](=[O:18])[CH:17]=2)[C:13]([O:15][CH2:33][O:34][CH3:35])=[O:14])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 30219833-Pyridinecarboxylic acid, 1,4-dihydro-6-(4-(dimethylamino)phenyl)-1-(4-hydroxyphenyl)-4-oxo-

Product 2

HCID 14010791HCID 14010791, compoundHCID 14010792HCID 14010792, compound

Conditions

Temperature
100 °C

Procedure

In 15 ml of N,N-dimethylformamide was dissolved 0.4 g of 6-(4-dimethylaminophenyl)-1-(4-hydroxyphenyl)-4-oxo-1,4-dihydronicotinic acid at room temperature, and to this solution was added 0.33 g of potassium carbonate. The resulting mixture was heated to 100° C. for 1 hour. The reaction mixture thus obtained was cooled to room temperature, and 0.2 g of methoxymethyl chloride was added thereto. The resulting mixture was subjected to reaction at room temperature for 1 hour. After completion of this reaction, 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 (30:1 by volume) mixture) to obtain 0.16 g of methoxymethyl 6-(4-dimethylaminophenyl)-1-(4-methoxymethyloxyphenyl)-4-oxo-1,4-dihydronicotinate having a melting point of 199°-201° C. and 0.13 g of methoxymethyl 6-(4-dimethylaminophenyl)-1-(4-hydroxyphenyl)-4-oxo-1,4-dihydronicotinate having a melting point of 211°-213° C.

Workup

  1. customThe reaction mixture thus obtained
  2. temperaturewas cooled to room temperature
  3. customThe resulting mixture was subjected to reaction at room temperature for 1 hour
  4. customAfter completion of this reaction
  5. customthe solvent was removed by distillation under reduced pressure
  6. customthe residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform/ethanol (30:1 by volume) mixture)

Sources & evidence

ORD record
ord-f276755255e0453b82595294c2759489
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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