Ethanol → 4-Ethoxyquinolin-8-amine

HRID 1469783Notes

Reaction equation

HRID 1469783 reaction equation
[H-].[Na+].Cl[C:4]1[C:13]2[C:8](=[C:9]([NH2:14])[CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1.[CH2:15]([OH:17])[CH3:16]>>[CH2:15]([O:17][C:4]1[C:13]2[C:8](=[C:9]([NH2:14])[CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1)[CH3:16]

Participants

4

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 126042744-Chloroquinolin-8-amine

Product 1

HCID 682812844-Ethoxyquinolin-8-amine

Conditions

Temperature
110 °C

Procedure

To a solution of ethanol (5 mL) was added NaH (141 mg, 5.6 mmol, 95%) at 0° C. and the reaction mixture was stirred at rt for 30 min. before 4-chloroquinolin-8-amine (200 mg, 1.12 mmol) was added to the reaction mixture. Then the reaction mixture was heated in a sealed tube at 110° C. for 12 h before it was quenched with 1N HCl. Then the reaction mixture was extracted with chloroform and the organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 140 mg of the title product. MS [M+H]+: 189.15.

Workup

  1. additionwas added to the reaction mixture
  2. customwas quenched with 1N HCl
  3. extractionThen the reaction mixture was extracted with chloroform
  4. washthe organic layer was washed with brine
  5. customseparated
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-01231f72cbe841a5af7d5c1b193ca28b
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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