4-Aminopyridine → 3-Ethoxy-4-(pyridin-4-ylamino)cyclobut-3-ene-1,2-dione

HRID 1653691Notes

Reaction equation

HRID 1653691 reaction equation
C(O[C:4]1[C:5](=[O:12])[C:6](=[O:11])[C:7]=1[O:8][CH2:9][CH3:10])C.[NH2:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.CCOC(C)=O>C(O)C>[N:17]1[CH:18]=[CH:19][C:14]([NH:13][C:4]2[C:5](=[O:12])[C:6](=[O:11])[C:7]=2[O:8][CH2:9][CH3:10])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 8857Ethyl AcetateHCID 123228Diethyl squarate

Product 1

HCID 106803193-Ethoxy-4-(pyridin-4-ylamino)cyclobut-3-ene-1,2-dioneYield 10%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 3,4-diethoxy-3-cyclobutene-1,2-dione (5.00 g, 29.4 mmol) in absolute ethanol (100 mL) was added a suspension of 4-aminopyridine (2.77 g, 29.4 mmol) in ethanol (50 mL). The reaction mixture was refluxed for 4 hours then concentrated to give crude product. Chromatography (EtOAc) afforded 0.632 g (10%) of a white solid: mp 120°-125° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. concentrationthen concentrated
  3. customto give crude product

Sources & evidence

ORD record
ord-42aac30fe5e4470aaf47934e8d14d373
Source dataset
uspto-grants-1995_04
Patent number
US05403854

Reaction notes

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