1-Chloro-2,4-Dinitrobenzene → HCID 59799764, compound

HRID 2074452Notes

Reaction equation

HRID 2074452 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH3:14][N:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[CH2:20][CH2:21][NH2:22]>CCO>[N+:11]([C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[NH:22][CH2:21][CH2:20][CH:16]1[CH2:17][CH2:18][CH2:19][N:15]1[CH3:14])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 61-Chloro-2,4-DinitrobenzeneHCID 983882-(2-Aminoethyl)-1-methylpyrrolidine

Product 1

HCID 59799764HCID 59799764, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Chloro-2,4-dinitrobenzene 1 (1.00 g, 4.937 mmol) was dissolved in anhydrous EtOH (20 mL) in a small argon purged flask and warmed in an oil bath to 40° C. Addition of 2-(1-methylpyrrolidin-2-yl)ethanamine 30 (0.696 g, 5.431 mmol) occurred dropwise. The reaction was stirred at 65-70° C. for 24 hours. After cooling to room temperature the solvent was removed under reduced pressure and the resulting residue partitioned between H2O and ethyl acetate and 1M ammonium hydroxide solution added to adjust pH to 10. The mixture was transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with H2O, brine (twice), dried over magnesium sulphate, filtered and then concentrated. Recrystallization of the crude solid from EtOH yielded a yellow powder 31 (2,4-Dinitro-phenyl)-[2-(1-methyl-pyrrolidin-2-yl)-ethyl]-amine Yield: 0.979 grams (67.4%). 1H NMR (DMSO) 8-1.51-1.71 (m, 3H), 1.78-1.96 (2×m, 3H), 2.06-2.14 (m, 1H), 2.26 (s, 3H), 2.26-2.36 (m, 1H), 2.93-3.03 (m, 1H), 3.48-3.53 (m, 2H), 7.18 (d, 1H, J=9.6), 8.27 (dd, 1H, J=9.7, 2.7), 8.86 (d, 1H, J=2.8), 9.50 (br s, 1H); MS (ESI): 295 (MH+, 100%)

Workup

  1. temperatureAfter cooling to room temperature the solvent
  2. customwas removed under reduced pressure
  3. customthe resulting residue partitioned between H2O and ethyl acetate and 1M ammonium hydroxide solution
  4. additionadded
  5. customThe mixture was transferred to a separatory funnel
  6. customthe organic layer collected
  7. extractionThe aqueous layer was further extracted with ethyl acetate
  8. washthe combined organic layers were washed with H2O, brine (twice),
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customRecrystallization of the crude solid from EtOH

Sources & evidence

ORD record
ord-f7f19a70efd8451eb8f20a9744382e77
Source dataset
uspto-grants-2011_04
Patent number
US07919510B2

Reaction notes

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