5-Aminoisoquinoline → 3-(Isoquinolin-5-ylamino)-4-ethoxy-cyclobut-3-ene-1,2-dione

HRID 1653693Notes

Reaction equation

HRID 1653693 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:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][N:18]=[CH:19]2>C(O)C>[CH:19]1[C:20]2[C:15](=[C:14]([NH:13][C:4]3[C:5](=[O:12])[C:6](=[O:11])[C:7]=3[O:8][CH2:9][CH3:10])[CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:17][N:18]=1

Participants

4

Reactant 2

HCID 707665-AminoisoquinolineHCID 123228Diethyl squarate

Product 1

HCID 108018323-(Isoquinolin-5-ylamino)-4-ethoxy-cyclobut-3-ene-1,2-dioneYield 29.2%

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 5-aminoisoquinoline (4.24 g, 29.4 mmol) in ethanol (50 mL). The mixture was heated to reflux overnight and then filtered to yield 2.30 g (29%) of solid: mp 182(dec) ° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. filtrationfiltered

Sources & evidence

ORD record
ord-a4c4de4a36144dd2856055da41cff65d
Source dataset
uspto-grants-1995_04
Patent number
US05403854

Reaction notes

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