Acetoxyacetyl chloride → HCID 88920476, compound

To the solution of 5-methoxy-2-nitrobenzaldehyde (6 g, 0.33 mol) in EtOAc (100 mL) was added 20% PtO2/C (1.2 g, 20%) and NaOAc (1.2 g, 20%). The reaction was stirred under hydrogen at room temperature for 0.5 h. The mixture was filtered through a Celite pad, and the filtrate was dried over anhydrous Na2SO4. After filtration, the solution was cooled to −78° C., and to which was added DIPEA (6.4 g, 0.5 mol, 1.5 eq) and 2-chloro-2-oxoethyl acetate (4.5 g, 0.33 mol, 1.0 eq). The resulting mixture was gradually warmed up to room temperature and stirred overnight. The reaction mixture was washed with water twice, dried over Na2SO4 and evaporated most of the solvent in vacuum. Then the solid separating out was collected by filtration to give 2-(2-formyl-4-methoxyphenylamino)-2-oxoethyl acetate (5.6 g, yield: 71%) as a light yellow solid.

1. filtrationThe mixture was filtered through a Celite pad
2. dry with materialthe filtrate was dried over anhydrous Na2SO4
3. filtrationAfter filtration
4. temperaturethe solution was cooled to −78° C.
5. temperatureThe resulting mixture was gradually warmed up to room temperature
6. stirringstirred overnight
7. washThe reaction mixture was washed with water twice
8. dry with materialdried over Na2SO4
9. customevaporated most of the solvent in vacuum
10. customThen the solid separating out
11. filtrationwas collected by filtration

ORD record

ord-e34f4a5ca29c4351adfe90d5f453103a

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09340527B2