Propylamine → 6-Methoxy-2-(propylamino)quinoline-3-carbaldehyde

HRID 1620200Notes

Reaction equation

HRID 1620200 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][CH3:15])[CH:8]=2)[N:3]=1.[CH2:16]([NH2:19])[CH2:17][CH3:18]>C1COCC1>[CH3:15][O:14][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:19][CH2:16][CH2:17][CH3:18])[C:11]([CH:12]=[O:13])=[CH:10]2

Participants

4

Reactant 2

HCID 7852PropylamineHCID 6890792-Chloro-6-methoxyquinoline-3-carbaldehyde

Product 1

HCID 866698176-Methoxy-2-(propylamino)quinoline-3-carbaldehydeYield 101.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
160 °C

Procedure

To a stirred solution of 2-chloro-6-methoxyquinoline-3-carbaldehyde (1.50 g, 6.77 mmol) in THF (10 mL) in a 20 mL microwave vial equipped with a magnetic stirrer was added propan-1-amine (5.6 mL, 67.7 mmol) and the reaction mixture was stirred for 1.5 h at 160° C. under microwave irradiation. After cooling to RT, the volatiles were removed 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 a 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 to give 6-methoxy-2-(propylamino)quinoline-3-carbaldehyde SLA 28172 as an orange solid (1.68 g, 99% yield).

Workup

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

Sources & evidence

ORD record
ord-612270b5c9c2429f9c3fe18e5a578d5e
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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