ChemicalBook CAS DataBase List methyl 5-acetamido-2-methyl-benzoate

methyl 5-acetamido-2-methyl-benzoate synthesis

5synthesis methods

Product Name:methyl 5-acetamido-2-methyl-benzoate
CAS Number:91133-72-1
Molecular formula:C11H13NO3
Molecular Weight:207.23

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Yield:91133-72-1 88%

Reaction Conditions:

Stage #1: methyl 2-methyl-5-nitrobenzoatewith hydrogen;palladium(II) hydroxide/carbon in methanol at 20; for 20 h;
Stage #2: acetic anhydride in tetrahydrofuran at 20; for 3 h;

Steps:

6.2

Step 2:; To a solution of the crude methyl ester 6-2 from step 1 (-55. 2 mmol) in MeOH (200 mL), Pearlman's catalyst (20% palladium hydroxide on carbon, 1.0 g) was added and the mixture was stirred under an atmosphere of H2 for 20 h at RT. The mixture was filtered through Celite and concentrated to dryness. The residue was re-dissolved in THF (200 mL), Ac2O (6.2 mL, 66 mmol) was added and the solution was stirred at RT for 3 h. The reaction mixture was concentrated to dryness under vacuum and the residue was re-dissolved in minimum volume of t-Bu methyl ether (-150 mL). The ether suspension was stirred at RT for 1 h before hexane (-100 mL) was added to precipitate the desired acetylated intermediate as a white solid. The solid was washed with hexane and dried to give the acetylated compound 6-3 in high purity (10.1 g, 88% yield).

References:

WO2005/80388,2005,A1 Location in patent:Page/Page column 55