Nitrogen → 2-Amino-5-benzylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

A suspension of active Zn metal in THF (0.76 M, 6.3 mL calculated to contain 4.8 mmol or a 20% theoretical excess) was placed in a thoroughly dried three-necked flask which was flushed continuously with a gentle stream of dry N2. A solution of 3,4-dichlorobenzyl chloride (790 mg, 4 mmol) in dry THF (2 mL) was then added slowly to the flask at room temperature, and the reaction mixture was stirred at 68° C. for 10 h and left to stand for 3 h to allow the excess Zn metal to settle to the bottom. The dark-brown solution of organozinc reagent was transferred via a cannula using gentle N2 pressure into another three-necked flask, to which was then added dropwise a solution of 9 (244 mg, 1 mmol) in dry THF (1 mL). Standard workup as for 10a afforded 10e as a pale-yellow powder (172 mg; 65%): mp 104-107° C.; 1H NMR (CDCl3) δ 3.80 (s, 2H, CH2), 4.35 (br s, 2H, NH2), 6.68 (d, J=8.4 Hz, 1H-3), 6.97 (dd, J=8.0 Hz, 2.0 Hz, 1H, H-6′), 7.11 (s, J=8.4 Hz, H-4), 7.16 (s, 1H, H-6), 7.22 (d, J=2.0 Hz, 1H, H-2), 7.35 (d, J 8.0 Hz, 1H, H-5′).

Provenance & Evidence