Pyrrolidine → HCID 389491, compound

HRID 5978Notes

Reaction equation

HRID 5978 reaction equation
Br[C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>>[CH3:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]([N+:12]([O-:14])=[O:13])=[C:2]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:7]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 2233701-Bromo-5-methyl-2,4-dinitrobenzene

Product 1

HCID 389491HCID 389491, compound

Procedure

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.

Workup

  1. temperaturewas heated at 90°-100° C. for 2 hours
  2. filtrationthe precipitated solids filtered off
  3. washwashed with water, and vacuum
  4. customdried
  5. customPurification
  6. customEvaporation of the eluants

Sources & evidence

ORD record
ord-b9a26e58d0284adca803900d4bbf0d32
Source dataset
uspto-grants-1993_09
Patent number
US05246955

Reaction notes

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