Water → N-(3-(3-Pyridyl)phenyl)-2-nitro-4-(1-pyrrolyl)aniline

HRID 1075457Notes

Reaction equation

HRID 1075457 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)[CH:7]=[CH:6][C:5]=1F)([O-:3])=[O:2].[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=2)[NH2:25])[CH:17]=1.O.[OH-].[Na+]>CN1CCCC1=O>[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[CH:23]=[C:24]([NH:25][C:5]3[CH:6]=[CH:7][C:8]([N:10]4[CH:14]=[CH:13][CH:12]=[CH:11]4)=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])[CH:26]=[CH:27][CH:28]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 4595213-(Pyridin-3-yl)anilineHCID 541021862-Nitro-4-(1-pyrrolyl)fluorobenzene

Product 1

HCID 54302123N-(3-(3-Pyridyl)phenyl)-2-nitro-4-(1-pyrrolyl)aniline

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
127.5 °C

Procedure

A mixture of 1a (0.5g, 2.4mmol) and 2a (0.41g, 2.4mmol) in N-methyl-2-pyrrolidone (2.5ml) is heated to 120-135° C. for 2 days. After cooling water and diluted sodium hydroxide is added and the mixture is extracted with ethyl acetate. The extract is dried over sodium sulfate, and the solvent is evaporated to leave crude 3a. This crude product is purified by column-chromatography on silica gel using dichloromethane and subsequently a mixture of dichloromethane and methanol (9:1) as the eluents to yield pure 3a (0.61g, 71%) as an oil.

Workup

  1. additionis added
  2. extractionthe mixture is extracted with ethyl acetate
  3. dry with materialThe extract is dried over sodium sulfate
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-d4c1f3c7dba84c46b09e982af156c5dd
Source dataset
uspto-grants-1999_05
Patent number
US05902813

Reaction notes

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