Ammonia → HCID 16495154, compound

Participants

Reaction Steps

A mixture of 6-methyl-pyridine-2-carboxaldehyde (500 mg), titanium (IV) isopropoxide (2.14 g), 2M ethylamine (in THF) in dry THF (12 mL) was stirred for 8 h at RT under nitrogen. Then NaBH4 (428 mg) and EtOH (4 mL) were added, the stirring at RT was continued for 7 h. The reaction mixture was then poured into aqueous ammonia (2M), the resulting inorganic precipitate was filtered and washed with ether. The organic layer was separated and the remaining aqueous layer was extracted with ether. The combined organic extracts were washed with 1M HCl to separate the neutral materials. The acidic aqueous solution was washed once with ether to separate the non-basic impurities, then treated with 2M NaOH to pH 10-12, and extracted with DCM (3×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give 100 mg (16%) of the title compound which was used for the next step without further purification.

Provenance & Evidence