3-Aminoquinoline → HCID 10706995, compound

HRID 1653696Notes

Reaction equation

HRID 1653696 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=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:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:2]([NH:1][C:16]2[C:17](=[O:22])[C:18](=[O:19])[C:15]=2[O:14][CH2:12][CH3:13])[CH:3]=1

Participants

4

Reactant 2

HCID 113753-AminoquinolineHCID 123228Diethyl squarate

Product 1

HCID 10706995HCID 10706995, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-aminoquinoline (2.12 g, 14.69 mmol) in ethanol (60 mL) was added 3,4-diethoxy-3-cyclobutene-1,2-dione (2.50 g, 14.69 mmol) and the resulting mixture was heated to reflux for 24 hours. The mixture was cooled, filtered, and the product was washed with diethylether and dried in vacuo to give 3.14 g (80%) of yellow solid which was used without purification: 1H NMR (DMSO-d6) δ11.14 (s, 1H), 8.92 (dd, 1H), 8.20 (dd, 1H), 7.90 (m, 2H), 7.63 (m, 2H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 24 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washthe product was washed with diethylether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-144aa30f4f9f4624815c9dce2d0235ec
Source dataset
uspto-grants-1995_04
Patent number
US05403854

Reaction notes

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