3-(4-Pyridyl)aniline → 3-[3-(4-Pyridyl)Anilino]-3-Cyclobutene-1,2-Dione

HRID 322066Notes

Reaction equation

HRID 322066 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C([O:18][C:19]1[C:20](=[O:24])[C:21](=O)[CH:22]=1)CCC>C(O)C>[N:11]1[CH:12]=[CH:13][C:8]([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[NH:1][C:21]2[C:20](=[O:24])[C:19](=[O:18])[CH:22]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 4595233-(4-Pyridyl)anilineHCID 157231823-Butoxycyclobut-3-ene-1,2-dione

Product 1

HCID 98378313-[3-(4-Pyridyl)Anilino]-3-Cyclobutene-1,2-DioneYield 76.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(3-aminophenyl)pyridine (0.81 g) and 3-n-butoxy-3-cyclobutene-1,2-dione (0.73 g) in ethanol (20 ml) is stirred at ambient temperature for 15 hours. The resultant precipitated solid is washed with methanol and ether and recrystallized from dimethyl formamide to give 0.91 g of the title compound, mp 252-255.5° C.

Workup

  1. customThe resultant precipitated solid
  2. washis washed with methanol and ether
  3. customrecrystallized from dimethyl formamide

Sources & evidence

ORD record
ord-f402d218b9ee48c28e8843565ed69c3d
Source dataset
uspto-grants-2001_04
Patent number
US06211220B1

Reaction notes

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