Pyrrolidine → HCID 389491, compound

Participants

Reaction Steps

A mixture of 5-bromo-2,4-dinitrotoluene (2.61 g, 10 mmol) and pyrrolidine (2.49 g, 35 mmol) was heated at 90°-100° C. for 2 hours. The resulting dark brown oil was combined with cracked ice and the precipitated solids filtered off, washed with water, and vacuum dried. Purification was carried out by flash chromatography of the solids on a silica gel column using chloroform/hexane (50:50) as eluant. Evaporation of the eluants afforded 10 as orange needles: 2.0 g (82%) yield; mp 142° C.; TLC (chloroform), Rf =0.82; IR (KBr pellet) 1606, 1566, 1510, 1369, 1350, 1334, 1301, 1276, 1130, 833 cm-1 ; 1H NMR (dimethyl sulfoxide-d6) 8.83 and 8.53 (2 H, 2×s, aromatic protons), 3.27 (4 H, m, methylenes adjacent to pyrrolidine N), 2.61 (3 H, s, methyl), 1.99 (4 H, m, other pyrrolidine methylenes); mass spectrum (EI mode) m/z 251 (P+), 234 (P+ -OH) Anal. Calcd for C11H13N3O4 ; C, 52.58; H, 5.21; N, 16.72. Found: C, 52.51; H, 5.27; N, 16.64.

Provenance & Evidence