Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Fluorophenylhydrazine hydrochloride | HCID 69981 | — |
| Reactant | 2-Chloro-5-(chloromethyl)pyridine | HCID 155479 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 86640698 | HCID 86640698 | — |
Reaction Steps
A mixture of (4-fluorophenyl)hydrazine hydrochloride (2.52 g, 20 mmol; Aldrich) and 2-chloro-5-(chloromethyl)pyridine (3.24 g, 20.00 mmol; Aldrich) in ethanol (120 mL) was treated with triethylamine (9.76 mL, 70.0 mmol; Aldrich), and the mixture was heated at 80° C. with stirring for 16 hours. The solvent was removed and the residue was purified by flash chromatography (silica gel, 10:1 CH2Cl2—CH3OH) to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 4.53 (s, 2H), 6.93-6.99 (m, 2H), 7.02-7.10 (m, 2H), 7.40 (d, J=8 Hz, 1H), 7.77 (dd, J=8, 3 Hz, 1H), 8.30 (d, J=3 Hz, 1H); MS (DCI/NH3) m/z 252 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09063126B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-4283b36b1bb848fcb1a3ec37e7934724 |
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| Source note | uspto-grants-2015_06 |
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