Ethylamine → 6-Ethoxy-2-(ethylamino)quinoline-3-carbaldehyde

HRID 1620209Notes

Reaction equation

HRID 1620209 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH2:15][CH3:16])[CH:8]=2)[N:3]=1.[CH2:17]([NH2:19])[CH3:18]>>[CH2:15]([O:14][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:19][CH2:17][CH3:18])[C:11]([CH:12]=[O:13])=[CH:10]2)[CH3:16]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 7886582-Chloro-6-ethoxyquinoline-3-carbaldehyde

Product 1

HCID 866698196-Ethoxy-2-(ethylamino)quinoline-3-carbaldehydeYield 101.7%

Conditions

Temperature
140 °C

Procedure

To a stirred solution of 2-chloro-6-ethoxyquinoline-3-carbaldehyde (298 mg, 1.26 mmol) in a 20 mL microwave vial equipped with a magnetic stirrer was added ethylamine (2.0 N in THF, 13.0 mL, 26.0 mmol) and the reaction mixture was stirred for 10 h at 140° C. under microwave irradiation then for 13 h at 130° C. still under microwave irradiation. After cooling to RT, the reaction mixture was concentrated to dryness at 40° C. under vacuum and the resulting yellow oil was taken up in a mixture of THF:1 N aq. HCl=1:1 (50 mL) and stirred for 1 h at RT. The volatiles were then removed at 40° C. under vacuum and the residue was then neutralised with saturated NaHCO3 aqueous solution before extraction with CH2Cl2 (100 mL). The organic phase was washed with brine (20 mL), dried over MgSO4, filtered, and concentrated under vacuum, which gave 6-ethoxy-2-(ethylamino)quinoline-3-carbaldehyde SLA 41034 as an orange solid (313 mg, >100% yield).

Workup

  1. customfor 13 h at 130° C. still under microwave irradiation
  2. temperatureAfter cooling to RT
  3. concentrationthe reaction mixture was concentrated to dryness at 40° C. under vacuum
  4. additionthe resulting yellow oil was taken up in a mixture of THF
  5. stirring1 N aq. HCl=1:1 (50 mL) and stirred for 1 h at RT
  6. customThe volatiles were then removed at 40° C. under vacuum
  7. extractionthe residue was then neutralised with saturated NaHCO3 aqueous solution before extraction with CH2Cl2 (100 mL)
  8. washThe organic phase was washed with brine (20 mL)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum, which

Sources & evidence

ORD record
ord-f095a5f0830a46b29ea71986054c092d
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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