Acetic Acid → HCID 23336273, compound

Under nitrogen atmosphere, zinc chloride (8.12 g, 59.6 mmol) and molecular sieve (200 mg) were taken in THF (10 ml) at room temperature. To the above mixture 3-nitrobenzaldehyde (3.00 g, 19.85 mmol), N-methylhydroxylamine hydrochloride (2.65 g, 31.8 mmol) and sodium bicarbonate (2.67 g, 31.8 mmol) were added. The mixture was stirred at room temperature for 30 min., followed by addition of 2-isocyano-2-methylpropane (3.30 g, 39.7 mmol) and acetic acid (3.58 g, 59.6 mmol) and the reaction mixture was stirred for 48 hrs. Water (50 ml) was added and the mixture was extracted with ethyl acetate (2×50 ml). Combined organic layer was washed with aq. satd. sodium bicarbonate solution and water and dried over sodium sulfate. The mixture was concentrated under vacuum and the crude product obtained was purified by column chromatography to afford the yellow oil (2.4 gm).

1. stirringthe reaction mixture was stirred for 48 hrs
2. extractionthe mixture was extracted with ethyl acetate (2×50 ml)
3. washCombined organic layer was washed with aq. satd
4. dry with materialsodium bicarbonate solution and water and dried over sodium sulfate
5. concentrationThe mixture was concentrated under vacuum
6. customthe crude product obtained
7. customwas purified by column chromatography

ORD record

ord-a5229e3b193542bdaeed7e325d5c9aad

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428499B2