Acetic Acid → HCID 18387472, compound

Participants

Reaction Steps

To acetic acid (25.76 ml, 450 mmol) and 2-(isopropylamino)ethanol (51.76 ml, 450 mmol) in dry THF (750 ml) at 0° C. was added 2-fluoro-5-nitrobenzaldehyde (75.88 g, 450 mmol) and sodium triacetoxyborohydride (141.99 g, 670 mmol) portionwise. The reaction was allowed to warm to room temperature and was stirred for 3 h. The mixture was taken up in acidic water and washed with methylene chloride (250 ml), made basic with 50% sodium hydroxide (150 ml) and extracted with methylene chloride (3×250 ml). The extracts were dried with magnesium sulfate, filtered, and concentrated to an oil. The oil was dissolved in 95% ethanol and treated with isopropanol-oxalic acid. The oxalate salt was collected by filtration (31.2 g, 20%), m.p. 106-107° C.

Provenance & Evidence