Methylamine → HCID 86669824, compound
Reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[CH:8]=[C:7]3[O:14][CH2:15][O:16][C:6]3=[CH:5][C:4]=2[N:3]=1.[CH3:17][NH2:18]>O1CCOCC1>[CH3:17][NH:18][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[CH:8]=[C:7]3[O:14][CH2:15][O:16][C:6]3=[CH:5][C:4]=2[N:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 160 °C
Procedure
To a stirred solution of 6-chloro[1,3]dioxolo[4,5-g]quinoline-7-carboxaldehyde (1.14 g, 4.84 mmol) in 1,4-dioxane (10 mL) in a 20 mL microwave vial equipped with a magnetic stirrer was added methylamine (40 wt. %, 4.0 mL, 46.2 mmol) and the reaction mixture was stirred for 25 min 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:2 N aq. HCl=1:1 (10 mL) and stirred for 20 min at RT. The volatiles were then removed at 40° C. under vacuum and the residue was then neutralised with a 10 N aqueous NaOH 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-(methylamino)-[1,3]dioxolo[4,5-g]quinoline-7-carbaldehyde CCH 34158-1 as a yellow solid (1.10 g, 99% 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
- stirring2 N aq. HCl=1:1 (10 mL) and stirred for 20 min at RT
- customThe volatiles were then removed at 40° C. under vacuum
- extractionthe residue was then neutralised with a 10 N aqueous NaOH solution before extraction 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-67791abf7d67458495f1053822ccb475
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772316B2
Reaction notes
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