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

HRID 2242045Notes

Reaction equation

HRID 2242045 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-814472ea39ec4781925da15ab276aa24
Source dataset
uspto-grants-2010_03
Patent number
US07671063B2

Reaction notes

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