Ethylamine → 2-(Ethylamino)-6-methoxyquinoline-3-carbaldehyde
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]([NH2:18])[CH3:17]>C1COCC1>[CH2:16]([NH:18][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)[CH3:17]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 160 °C
Procedure
To a stirred solution of 2-chloro-6-methoxyquinoline-3-carbaldehyde (1.51 g, 6.80 mmol) in THF (10 mL) in a 20 mL microwave vial equipped with a magnetic stirrer was added ethylamine (2 M in THF, 33.8 mL, 67.6 mmol) and the mixture was stirred at 160° C. for 6 h under microwave irradiation. After cooling to RT, the volatiles were removed under vacuum at 40° C. and the resulting yellow oil was taken up in a mixture of THF:1 N aq. HCl=1:1 (50 mL) and stirred for 15 min at RT. THF was removed at 40° C. under vacuum and the residue was then neutralised with a saturated NaHCO3 aqueous solution before to be extracted with CH2Cl2 (100 mL). The organic phase was washed with brine (20 mL), dried over MgSO4, filtered, and concentrated at 40° C. under vacuum to give 2-(ethylamino)-6-methoxyquinoline-3-carbaldehyde SLA 28162 as an orange oil (1.19 g, 76% yield).
Workup
- temperatureAfter cooling to RT
- customthe volatiles were removed under vacuum at 40° C.
- additionthe resulting yellow oil was taken up in a mixture of THF
- stirring1 N aq. HCl=1:1 (50 mL) and stirred for 15 min at RT
- customTHF was removed at 40° C. under vacuum
- extractionto be extracted with CH2Cl2 (100 mL)
- washThe organic phase was washed with brine (20 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated at 40° C. under vacuum
Sources & evidence
- ORD record
- ord-9646a70b5ce7485ca8e04d2a2db01c29
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772316B2
Reaction notes
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