Benzylamine → HCID 22034114, compound

Participants

Reaction Steps

2,4-Dichloro-6-methyl-3-nitro-pyridine (2 g, 9.7 mmol) and triethylamine (1.35 mL, 9.7 mmol) were dissolved in 40 mL THF and cooled (ice/water) to ˜5° C. A solution of benzylamine (1.04 g, 9.7 mmol) in 10 mL THF was added dropwise and the mixture was then allowed to warm gradually to room temperature overnight. The mixture was evaporated in vacuo, partitioned between EtOAc (50 mL) and water (20 mL). The organic layer was washed with saturated aqueous NaHCO3 (10 mL), dried (MgSO4) and evaporated in vacuo to an orange gum. This gum was preabsorbed onto silica gel and then purified by column chromatography, eluting with DCM:pentane 3:1. Appropriate fractions combined and evaporated in vacuo to yield the title compound as a yellow solid (716 mg).

Provenance & Evidence