N-Benzyl-N,2-dimethyl-5-nitro-aniline → HCID 55091508, compound

HRID 2061440Notes

Reaction equation

HRID 2061440 reaction equation
[CH2:1]([N:8]([CH3:19])[C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.Cl>[CH2:1]([N:8]([CH3:19])[C:9]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 66915963N-Benzyl-N,2-dimethyl-5-nitro-aniline

Product 1

HCID 55091508HCID 55091508, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

SnCl2-dihydrate (1117 mg, 4.95 mmol) is added to a solution of N-Benzyl-N,2-dimethyl-5-nitro-aniline (247 mg, 0.96 mmol) in methanol (10 mL) and conc. HCl (1 mL). After boiling under reflux for 2.5 h, volatiles are evaporated under reduced pressure and the residue is partitioned between EtOAc and water, the pH being adjusted to approx. 10 by the addition of 2N NaOH. The organic layer is washed with sat. brine, dried (Na2SO4), and evaporated. Chromatography of the residue (silica gel, hexanes/EtOAc 3:2) yields N3-benzyl-N3,4-dimethyl-benzene-1,3-diamine.

Workup

  1. temperatureunder reflux for 2.5 h
  2. customvolatiles are evaporated under reduced pressure
  3. customthe residue is partitioned between EtOAc and water
  4. additionby the addition of 2N NaOH
  5. washThe organic layer is washed with sat. brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-08d945441edc49bbbab1c9577b101778
Source dataset
uspto-grants-2012_10
Patent number
US08283356B2

Reaction notes

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