Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanolamine | HCID 700 | — |
| Reactant | Quinaldic Acid | HCID 7124 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | Isobutyl chloroformate | HCID 62365 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 4319814 | HCID 4319814 | 90% |
Reaction Steps
To an oven dried 250 mL round bottomed flask was weighed quinaldic acid (1.734 g, 10.0 mmol). A magnetic stir bar was added and the flask was put under N2 atmosphere. The flask was charged with DCM (100 mL) and cooled to 0° C. in an ice bath. The flask was then charged with N-methyl morpholine (1.44 mL, 15.0 mmol) and isobutlychloroformate (1.51 mL, 11.5 mmol) via syringe addition. The reaction was allowed to stir at 0° C. for 20 min until the solution became cloudy. At which point freshly distilled ethanolamine (695 uL, 11.5 mmol) was added slowly to the flask via syringe. The reaction mixture was allowed to slowly warm to room temperature to form N-(2-hydroxyethyl)quinoline-2-carboxamide was formed according to the formula
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08263774B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-d65367be521042cb9b0b807276c48ed6 |
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| Source note | uspto-grants-2012_09 |
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