Реакция #6074

Уравнение реакции

5-bromo-2,4-dinitrotoluene

pyrrolidine

→

17

2,4-Dinitro-5-N-pyrrolidinotoluene

Условия реакции

Обработка

1. 1
   Температураwas heated at 90°-100° C. for 2 hours
2. 2
   Фильтрацияthe precipitated solids filtered off
3. 3
   Промывкаwashed with water, and vacuum
4. 4
   Другоеdried
5. 5
   ДругоеPurification
6. 6
   ДругоеEvaporation of the eluants

Методика

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 17 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) δ8.83 and 8 53 (2H, 2×s, aromatic protons), 3.27 (4H, m, methylenes adjacent to pyrrolidine N), 2.61 (3H, s, methyl), 1.99 (4H, 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.

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