Pyrrolidine → 2-Nitro-5-(1-pyrrolidinyl)aniline

HRID 1888951Notes

Reaction equation

HRID 1888951 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>>[N+:9]([C:5]1[CH:4]=[CH:3][C:2]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:8][C:6]=1[NH2:7])([O-:11])=[O:10]

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 27602392-Nitro-5-(1-pyrrolidinyl)anilineYield 93%

Procedure

A mixture of 5-chloro-2-nitroaniline (1.73 g, 10 mmol) and pyrrolidine (1.42 g, 20 mmole) was refluxed in a pressure vessel for 6 h. Solvent was evaporated and the residue was diluted with ethyl acetate. The resulting mixture was washed with aqueous NaHCO3 (5%) and distilled water, dried over MgSO4, and concentrated to afford 2-nitro-5-(pyrrolidin-1-yl)benzenamine as a solid (93% yield). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.80 (d, J=8 Hz, 1H, 3-H), 7.22 (s, 2H, NH2), 6.05 (dd, J=8, 2 Hz, 1H, 4-H), 5.81 (d, J=2 Hz, 1H, 6-H), 3.30-3.27 (m, 4H, 2′,5′-H), 1.97-1.91 (m, 4H, 3′,4′-H). 13C NMR (100 MHz, CDCl3-d1) δ (ppm): 151.9, 148.3, 127.4, 122.1, 104.7, 94.5, 47.3, 47.3, 24.8, 24.8; EIMS: m/z 207 (M+).

Workup

  1. temperaturewas refluxed in a pressure vessel for 6 h
  2. customSolvent was evaporated
  3. additionthe residue was diluted with ethyl acetate
  4. washThe resulting mixture was washed with aqueous NaHCO3 (5%)
  5. distillationdistilled water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-13af7000c5cf48b0b1a2abe514f2f196
Source dataset
uspto-grants-2013_08
Patent number
US08501957B2

Reaction notes

Loading…