Hydrochloric Acid → 5-Nitro-2-(1-pyrrolidinyl)benzenamine

HRID 349734Notes

Reaction equation

HRID 349734 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:8]([NH:10]C(=O)C)[CH:9]=1)([O-:3])=[O:2].Cl.[OH-].[Na+]>C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:8]([CH:9]=1)[NH2:10])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 609964HCID 609964, compound

Product 1

HCID 129083915-Nitro-2-(1-pyrrolidinyl)benzenamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.58 g (2.3 mmol) of N-(5-nitro-2-pyrrolidin-1-ylphenyl)acetamide was admixed with 12 ml of conc. hydrochloric acid and heated to reflux for 1.5 hours. The solution was added to 100 ml of ice/water, neutralized with 2 N sodium hydroxide solution and admixed three times with ethyl acetate. After the mixture had been dried, the solvent was distilled off under reduced pressure to obtain the product quantitatively as a red solid which was used for the reactions a-d described in Example 1 without further purification (reaction with the acyl isocyanate, reduction with SnCl2 and acylation with Ac2O).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 hours
  3. customAfter the mixture had been dried
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto obtain the product quantitatively as a red solid which
  6. customdescribed in Example 1 without further purification (
  7. customreaction with the acyl isocyanate, reduction with SnCl2 and acylation with Ac2O)

Sources & evidence

ORD record
ord-c211579ec17544f3acd4387814493215
Source dataset
uspto-grants-2007_02
Patent number
US07179941B2

Reaction notes

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