2-amino-2-(4-methoxyphenyl)acetamide synthesis

5synthesis methods

Product Name:2-amino-2-(4-methoxyphenyl)acetamide
CAS Number:76986-15-7
Molecular formula:C9H12N2O2
Molecular Weight:180.2038

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Yield:76986-15-7 12%

Reaction Conditions:

Stage #1: 2-(4-methoxyphenyl)glycinewith thionyl chloride in methanol at 0; for 3.5 h;Heating / reflux;
Stage #2: with ammonia in water at 20;

Steps:

12 2-Amino-2-[4-(methyloxy)phenyl]acetamide

To an ice-cold suspension of 4-methoxyphenylglycine (3.77 g; 0.021 mol) in methanol was added thionyl chloride dropwise over 30 min. After complete addition, the reaction mixture was heated at reflux for 3 h, cooled and evaporated. The resulting solid was dissolved in 0.88 ammonia (100 ml) and stirred at room temperature overnight. The reaction was extracted twice with DCM and the organic phases separated with a Phase-Separation cartridge and evaporated under reduced pressure to afford the title product (0.45 g; 12%) as a white solid. ¹H NMR (CDCl₃) δ: 1.77 (2H, br s), 3.80 (3H, s), 4.50 (1H, s), 5.52 (1H, s), 6.83 (1H, s), 6.87-6.91 (2H, m), 7.33-7.36 (2H, m).

References:

US2008/221185,2008,A1 Location in patent:Page/Page column 27