Sodium Hydroxide → 3-(2-Dimethylaminoethylcarbamoyl)-2-methyl-4-(3-nitrophenyl)-6-phenylpyridine

HRID 1722777Notes

Reaction equation

HRID 1722777 reaction equation
[CH3:1][C:2]1[C:7]([C:8](O)=[O:9])=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[CH:5]=[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:3]=1.S(Cl)(Cl)=O.[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][NH2:34].[OH-].[Na+]>C(Cl)Cl.O.CN(C)C=O>[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][NH:34][C:8]([C:7]1[C:2]([CH3:1])=[N:3][C:4]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:5][C:6]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)=[O:9]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 66053N,N-DimethylethylenediamineHCID 104720472-Methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylic acid

Product 1

HCID 104089363-(2-Dimethylaminoethylcarbamoyl)-2-methyl-4-(3-nitrophenyl)-6-phenylpyridineYield 36.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent4×

Procedure

To a mixture of 2-methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylic acid (1.98 g), methylene chloride (20 ml) and N,N-dimethylformamide (4 ml) was added a solution of thionyl chloride (0.47 ml) in methylene chloride (2 ml) at 7° C. under ice cooling. After stirring for 2.5 hours at the same condition, a solution of 2-dimethylaminoethylamine (1.3 g), in methylene chloride (20 ml) was added thereto and stirred for 2 hours at the same temperature. After adding water (150 ml) and methylene chloride (150 ml) thereto, the mixture was adjusted to pH 9.0 with 10% aqueous sodium hydroxide. The organic layer was separated, washed successively with water and saturated brine, dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to a column chromatography on alumina (70 g) and eluted with chloroform. The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was recrystallized from diethyl ether to give 3-(2-dimethylaminoethylcarbamoyl)-2-methyl-4-(3-nitrophenyl)-6-phenylpyridine (0.88 g).

Workup

  1. stirringstirred for 2 hours at the same temperature
  2. customThe organic layer was separated
  3. washwashed successively with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. washeluted with chloroform
  7. additionThe fractions containing the object compound
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-778462e419fa47fe87c5da92dfa264e6
Source dataset
uspto-grants-1989_08
Patent number
US04857527

Reaction notes

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