3-(Pyridin-3-yl)aniline → HCID 11325073, compound

HRID 581973Notes

Reaction equation

HRID 581973 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7](F)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)=[O:3].[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=2)[NH2:23])[CH:15]=1.C([O-])(O)=O.[Na+]>CN1CCCC1=O>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:23][C:22]2[CH:24]=[CH:25][CH:26]=[C:20]([C:16]3[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=3)[CH:21]=2)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 4595213-(Pyridin-3-yl)anilineHCID 516892Sodium BicarbonateHCID 27346124'-Fluoro-3'-nitroacetophenone

Product 1

HCID 11325073HCID 11325073, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 4-Fluoro-3-nitroacetophenone (5 g, 27.3 mmol) and 3-(3-pyridyl)aniline (4.62 g, 27.2 mmol) in dry 1-methyl-2-pyrrolidone (10 ml) is stirred at 40-50° C. overnight. The resulting solid reaction mixture is suspended in ice water (50 ml) and made alkaline by addition of 1 M NaHCO3. The product is filtered off, washed with water and dried to yield 7.68 g 4-acetyl-2-nitro-N-(3-(3-pyridyl)phenyl)aniline (85%).

Workup

  1. customThe resulting solid reaction mixture
  2. filtrationThe product is filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-2bae8e747a4e40458a97c8e9bbf1dbbb
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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