4-Nitrodiphenylamine → N-Phenyl-p-phenylenediamine

HRID 1665648Notes

Reaction equation

HRID 1665648 reaction equation
[Cl-].[NH4+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)([O-])=O>O.C1COCC1.[Zn]>[C:13]1([NH:12][C:9]2[CH:10]=[CH:11][C:6]([NH2:3])=[CH:7][CH:8]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 2

HCID 132714-NitrodiphenylamineHCID 25517Ammonium Chloride

Product 1

HCID 7564N-Phenyl-p-phenylenediamine

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ammonium chloride (48 mg, 9 mmol) in water (1 mL) was added to a stirred solution of (4-nitro-phenyl)-phenyl-amine (200 mg, 0.9 mmol) in THF (4 mL). Zinc powder (48 mg, 7.4 mmol) was then added portion wise and the resulting mixture was stirred at room temperature for 2 hours then filtered over celite. The filtrate was extracted with ethyl acetate and the ethyl acetate was washed with brine solution, dried over Na2SO4 and concentrated to 160 mg (96%) of N-phenyl-benzene-1,4-diamine. LCMS: 185.1 (M+1)+, 93.9%, 1H NMR: (DMSO-d6): 67.2 (t, 2H), 7.0 (d, 2H), 6.8 (m, 2H), 6.7 (d, 2H).

Workup

  1. filtrationthen filtered over celite
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washthe ethyl acetate was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to 160 mg (96%) of N-phenyl-benzene-1,4-diamine

Sources & evidence

ORD record
ord-1ff72835b37740c7b169f90dfb029c2f
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

Loading…