Methylamine → 6-Methoxy-2-(methylamino)quinoline-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.[CH3:16][NH2:17]>O1CCOCC1>[CH3:15][O:14][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:17][CH3:16])[C:11]([CH:12]=[O:13])=[CH:10]2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 160 °C
Procedure
To a stirred solution of 2-chloro-6-methoxyquinoline-3-carbaldehyde (1.50 g, 6.77 mmol) in 1,4-dioxan (10 mL) in a 20 mL microwave vial equipped with a magnetic stirrer was added methylamine (40 wt % solution in water, 2.10 mL, 24.3 mmol) and the reaction mixture was stirred for 6 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. 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 under vacuum, to give 6-methoxy-2-(methylamino)quinoline-3-carbaldehyde SLA 28150 as an orange oil (1.44 g, 98% yield).
Workup
- temperatureAfter cooling to RT
- customthe volatiles were removed at 40° C. under vacuum
- additionthe resulting yellow oil was taken up in a mixture of THF
- stirring1 N aq. HCl=1:1 (50 mL) and stirred for 1 h 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 under vacuum
Sources & evidence
- ORD record
- ord-0f3fb6519888473c9e09461f52d15de5
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772316B2
Reaction notes
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