Water → 2-Nitro-4-(1-pyrrolidinyl)benzenamine

HRID 2093050Notes

Reaction equation

HRID 2093050 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[NH:15]C(=O)C)([O-:3])=[O:2].O.[OH-].[Na+]>CO>[N+:1]([C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[NH2:15])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 66863819HCID 66863819, compound

Product 1

HCID 216537832-Nitro-4-(1-pyrrolidinyl)benzenamineYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(2-nitro-4-pyrrolidin-1-ylphenyl)acetamide obtained in step IV above (1.0 eq) in MeOH and water was added NaOH (1.5 eq) at room temperature and stirred for 5 hrs. Water was added to the reaction mixture and the organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the desired 2-nitro-4-pyrrolidin-1-ylaniline. (Yield=85%)

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto afford crude product, which
  5. customon purification by column chromatography

Sources & evidence

ORD record
ord-808e9c0d5f9a486495ed68ce6558f69d
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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