Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 3-Chloro-2-fluoroaniline | HCID 75014 | — |
| Reactant | 1H-Imidazole-4-carbaldehyde | HCID 76428 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 62761381 | HCID 62761381 | 81% |
Reaction Steps
To a solution of 3-chloro-2-fluoroaniline (0.44 g, 3 mmol) in methanol (5 ml) was added 4-formylimidazole (0.29 g, 3 mmol). After stirring the mixture overnight at 60° C. the solution was cooled and sodium borohydride (0.57 g, 15 mmol) was added. The reaction mixture was stirred at room temperature for 4 hours. Then water was added and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water, dried over magnesium sulfate and evaporated. The residue was purified by column filtration (heptane/ethyl acetate=1:1) to yield a light yellow liquid (0.55 mg, 81%); MS (ISP): 226.3 ((M+H)+.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08586617B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-4ec243d0d1824efabf70784fbff1ef4d |
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| Source note | uspto-grants-2013_11 |
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