Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethylamine | HCID 6341 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 6-Chloro-[1,3]dioxolo[4,5-g]quinoline-7-carbaldehyde | HCID 847400 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86669826 | HCID 86669826 | 91% |
Reaction Steps
To a solution of 6-chloro-[1,3]dioxolo[4,5-g]quinoline-7-carbaldehyde (1.0 g, 4.24 mmol) in dioxane (10 mL) was added ethylamine (3.58 mL, 70% in water) and the mixture was heated at 160° C. under microwave irradiation for 45 min. After cooling to RT, the mixture was poured into a mixture of THF:1 N HCl aq. solution=1:1 (25 mL) and stirred for 25 min at RT. The mixture was brought to pH=7 with a saturated aq. solution of NaHCO3 and extracted with CH2Cl2 (50 mL). The organic layer was washed with H2O (3×30 mL), brine (30 mL), dried over Na2SO4, filtered and evaporated to give 6-(ethylamino)-[1,3]dioxolo[4,5-g]quinoline-7-carbaldehyde RBO 35180 as a yellow solid (941 mg, 91% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08772316B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-e16f2486fbe84223898639d9a9b7cc22 |
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| Source note | uspto-grants-2014_07 |
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