8-Aminoquinoline → HCID 10516031, compound

HRID 1653695Notes

Reaction equation

HRID 1653695 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH2:12]([O:14][C:15]1[C:16](=O)[C:17](=[O:22])[C:18]=1[O:19]CC)[CH3:13]>C(O)C>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][C:16]2[C:17](=[O:22])[C:18](=[O:19])[C:15]=2[O:14][CH2:12][CH3:13])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 123228Diethyl squarate

Product 1

HCID 10516031HCID 10516031, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 8-aminoquinoline (1.00 g, 6.94 mmol) in ethanol (20 mL) was added 3,4-diethoxy-3-cyclobutene-1,2-dione (1.03 mL, 6.94 mmol) and the resulting mixture was heated to reflux for 24 hours. The mixture was cooled, diluted with ethanol, and filtered. The crude product was triturated with chloroform/hexanes, then purified by chromatography (EtOAc/hexane) to give 1.31 g (70%) of product: 1H NMR (DMSO-d6) δ9.75 (br m, 1H), 8.86 (dd, 1H), 8.26 (br m, 1H), 8.20 (dd, 1H), 7.57 (m, 2H), 7.53 (dd, 1H), 4.95 (q, 2H), 1.59 (t, 3H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 24 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customThe crude product was triturated with chloroform/hexanes
  6. custompurified by chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-60b652252b304ea3a860c8877d9a9383
Source dataset
uspto-grants-1995_04
Patent number
US05403854

Reaction notes

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