Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Ethylamine | HCID 6341 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | 3-Bromoquinoline-2-carbaldehyde | HCID 57355556 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 58579955 | HCID 58579955 | — |
Reaction Steps
3-Bromo-quinoline-2-carbaldehyde (3.34 g, 16.3 mmol), ethylamine (2M in MeOH; 9.78 mL, 19.6 mmol), and acetic acid (1.02 mL, 17.8 mmol) were combined in MeOH (25 mL) and stirred at 0° C. for 30 minutes. Sodium cyanoborohydride (1.53 g, 24.5 mmol) was added, and the reaction was monitored by analytical LCMS. The mixture was worked-up with saturated aqueous NaHCO3 and extracted with CH2Cl2, and the residue was purified by silica gel chromatography (0-5% MeOH in CH2Cl2) to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08378107B2 |
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| Source dataset | uspto-grants-2013_02 |
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| ORD ID | ord-2f31e7fc1565454ebb4fe7a01297dda9 |
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| Source note | uspto-grants-2013_02 |
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