1,1'-Carbonyldiimidazole → 2-(2-chloro-5-nitrophenyl)-N-methoxyacetamide

2-(2-Chloro-5-nitrophenyl)acetic acid (49.9 mmol) and CDI (59.9 mmol) were dissolved in DMF (300 mL) to give a yellow solution. O-Methylhydroxylamine hydrochloride (59.9 mmol) was added. The mixture was stirred at room temperature for 4 h. The reaction mixture was then concentrated under reduced pressure to approximately 50 mL and diluted with 300 mL of ethyl acetate. The organic layer was washed twice with 250 mL of water. The aqueous layer was then saturated with brine and back-extracted with ethyl acetate. The organic layers were combined and subsequently washed with 300 mL of 1 M aq. HCl, 300 mL of sat. aq. NaHCO3, and 300 mL of brine. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to give 2-(2-chloro-5-nitrophenyl)-N-methoxyacetamide as a solid (69%).

1. customto give a yellow solution
2. concentrationThe reaction mixture was then concentrated under reduced pressure to approximately 50 mL
3. additiondiluted with 300 mL of ethyl acetate
4. washThe organic layer was washed twice with 250 mL of water
5. extractionsaturated with brine and back-extracted with ethyl acetate
6. washsubsequently washed with 300 mL of 1 M aq. HCl, 300 mL of sat. aq. NaHCO3, and 300 mL of brine
7. customThe organic layer was separated
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under vacuum

ORD record

ord-0065af72ef5b440899df98e69cc16ce4

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232283B2