Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Butylamine | HCID 8007 | — |
| Reactant | 4-Chloro-7-fluoro-6-methoxy-3-quinolinecarbonitrile | HCID 12150703 | — |
| Solvent | Glycol monoethyl ether | HCID 8076 | — |
| Product | HCID 23498092 | HCID 23498092 | 66.3% |
Reaction Steps
A mixture of 4-chloro-7-fluoro-6-methoxy-3-quinolinecarbonitrile (300 mg, 1.27 mmol) and butylamine (205 mg, 2.80 mmol) in 10 mL of 2-ethoxyethanol is heated at 80° C. for 1.5 hours then cooled to room temperature. The reaction mixture is concentrated in vacuo and aqueous sodium bicarbonate is added to the residue. After stirring for 20 minutes, the solids are collected by filtration. Purification by preparative thin layer chromatography, eluting with 2% methanol in dichloromethane provides 230 mg of 4-butylamino-7-fluoro-6-methoxy-3-quinolinecarbonitrile, mp 155-156° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06780996B2 |
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| Source dataset | uspto-grants-2004_08 |
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| ORD ID | ord-a69c7fbb75f04b4e9c91c2181317344e |
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| Source note | uspto-grants-2004_08 |
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