3-Aminopyridine → 3-(Pyridin-3-ylamino)-4-ethoxy-cyclobut-3-ene-1,2-dione

HRID 1653692Notes

Reaction equation

HRID 1653692 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:15]=[N:16][CH:17]=[CH:18][CH:19]=1>C(O)C>[N:16]1[CH:17]=[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]=1

Participants

4

Reactant 2

HCID 100093-AminopyridineHCID 123228Diethyl squarate

Product 1

HCID 105129913-(Pyridin-3-ylamino)-4-ethoxy-cyclobut-3-ene-1,2-dioneYield 49.1%

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 3-aminopyridine (2.77 g, 29.4 mmol) in ethanol (50 mL). The mixture was heated at reflux for 18 hours, then concentrated. Chromatography (4:1 EtOAc/hexane) afforded 3.15 g (49%)of a white solid: mp 140°-145° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 hours
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b57b5905a8ce4a83a0a1390c5d0f4790
Source dataset
uspto-grants-1995_04
Patent number
US05403854

Reaction notes

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