Isopropylamine → 2-(Isopropylamino)-6-methoxyquinoline-3-carbaldehyde

HRID 1620232Notes

Reaction equation

HRID 1620232 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.[CH3:16][CH:17]([NH2:19])[CH3:18]>C1COCC1>[CH:17]([NH:19][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)([CH3:18])[CH3:16]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 6890792-Chloro-6-methoxyquinoline-3-carbaldehyde

Product 1

HCID 866698202-(Isopropylamino)-6-methoxyquinoline-3-carbaldehydeYield 99.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
180 °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-2-amine (5.76 mL, 67.7 mmol) and the reaction mixture was stirred for 12.5 h at 160° C. and finally 45 min at 180° 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 layer was washed with brine (20 mL), dried over MgSO4, filtered, and concentrated under vacuum to give 2-(isopropylamino)-6-methoxyquinoline-3-carbaldehyde SLA 28186 as an orange solid (1.64 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 layer was washed with brine (20 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c1885b70b7e5438fa4ebd0560a1d6e71
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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