Ethyl 2-aMino-2-(2-pyridinyl)acetate synthesis

Yield:55243-15-7 99%

Reaction Conditions:

with palladium on activated charcoal;hydrogen in methanol at 20; for 48 h;

Steps:

2.2 Ethyl 2-amino-2-(pyridin-2-yl) acetate (8)

4.2.2
Ethyl 2-amino-2-(pyridin-2-yl) acetate (8)
To a stirred solution of compound 7 (52.0 G, 267.7 mmol s) in methanol (1.5 L), Pd/C (10.0 g) was added.
Hydrogen pressure was applied by fixing the hydrogen filled balloon on the reaction vessel and the reaction mixture was stirred at r.t. for 48 h.
The reaction mass was filtered through celite and the filtrate was concentrated under reduced pressure to obtain compound 8 (48.4 g) as brown gummy mass in 99% yield. ¹H NMR (CDCl₃): δ 8.58 (d, J = 4.3 Hz, 1H), 7.69 (t, J = 7.6 Hz, 1H), 7.42 (d, J = 7.7 Hz, 1H), 7.24 (dd, J = 5.0, 7.1 Hz, 1H), 4.71 (s, 1H), 4.19 (q, J = 7.1 Hz, 2H), 2.14 (bs, 2H), 1.21 (t, J = 7.1 Hz, 3H).

References:

Nirogi, Ramakrishna;Mohammed, Abdul Rasheed;Shinde, Anil K.;Bogaraju, Narsimha;Gagginapalli, Shankar Reddy;Ravella, Srinivasa Rao;Kota, Laxman;Bhyrapuneni, Gopinadh;Muddana, Nageswara Rao;Benade, Vijay;Palacharla, Raghava Chowdary;Jayarajan, Pradeep;Subramanian, Ramkumar;Goyal, Vinod Kumar [European Journal of Medicinal Chemistry,2015,vol. 103,p. 289 - 301]