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Sodium Hydroxide → 4-Methyl-3-(4-methylpiperazin-1-ylcarbonyl)-2-(3-nitrophenyl)-6-phenylpyridine

HRID 981161
Notes
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Reaction equation

HRID 981161 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[C:23]([OH:25])=O.S(Cl)(Cl)=O.[CH3:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.[OH-].[Na+]>C(Cl)Cl.O.CN(C)C=O>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[C:23]([N:34]1[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]1)=[O:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 531671-MethylpiperazineHCID 103595154-Methyl-2-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylic acid

Product 1

HCID 99793004-Methyl-3-(4-methylpiperazin-1-ylcarbonyl)-2-(3-nitrophenyl)-6-phenylpyridineYield 55.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent4×

Procedure

To a mixture of 4-methyl-2-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylic acid (1.4 g), methylene chloride 14 ml) and N,N-dimethylformamide (2.8 ml) was added a solution of thionyl chloride (0.33 ml) in methylene chloride (3 ml) at 7° C. under ice cooling. After stirring for 2 hours at the same condition, a solution of 1-methylpiperazine (1.05 g) in methylene chloride (7 ml) was added thereto and the mixture was stirred for 2 hours at the same temperature. After adding Water (100 ml) and methylene chloride (50 ml) thereto, the mixture was adjusted to pH 8.5 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 recrystallized from a mixture of ethanol and diethyl ether to give 4-methyl-3-(4 methylpiperazin-1-ylcarbonyl)-2-(3-nitrophenyl)-6-phenylpyrid ine (0.97 g).

Workup

  1. stirringthe mixture was stirred 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. customThe residue was recrystallized from a mixture of ethanol and diethyl ether

Sources & evidence

ORD record
ord-cb53f3309e0144ffbf3e4d1dc517256f
Source dataset
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04990507

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes