Hydrochloric Acid → N-(2-Chloro-4-cyano-6-methylphenyl)acetamide

To a stirred solution of 4-amino-3-chloro-5-methylbenzonitrile (0.516 g, 3.1 mmol) in 10 mL of THF at room temperature was added 6.6 mL of 1.0 M NaHMDS in THF. The resulting reaction mixture was stirred at room temperature for 30 min., at which time acetyl chloride (3.1 mmol) was added. DCM (100 mL) and water (100 mL) were added to the reaction mixture after being stirred overnight, followed by the addition of 5 mL of 1.4 N HCl aqueous solution. Layers were separated and the aqueous layer was extracted with DCM (2×100 mL). The extracts were combined and solvents were evaporated in vacuo. The residue was purified by flash chromatography (5-20% EtOAc/DCM) to give 0.220 g of 4-acetamido-3-chloro-5-methylbenzonitrile. 1H NMR (500 MHz, CDCl3) δ 7.57 (s, 1 H), 7.46 (s, 1 H), 7.02 (s, 1 H), 2.31 (s, 3 H), 2.26 (s, 3 H).

1. customThe resulting reaction mixture
2. additionwas added
3. customLayers were separated
4. extractionthe aqueous layer was extracted with DCM (2×100 mL)
5. customsolvents were evaporated in vacuo
6. customThe residue was purified by flash chromatography (5-20% EtOAc/DCM)

ORD record

ord-3fe4dab1c56147089ed38a8f368e6288

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07273882B2