Ethanol → ((1-Naphthyl)methyl)(2-amino-4-methyl-phenyl)amine

HRID 916081Notes

Reaction equation

HRID 916081 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1.[CH2:12](O)[CH3:13].[OH-].[Na+].O1[CH2:22][CH2:21]OCC1>[Zn]>[C:12]1([CH2:13][NH:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=2[NH2:9])[C:21]2[C:22](=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 69784-Methyl-2-nitroanilineHCID 14798Sodium HydroxideHCID 312751,4-Dioxane

Product 1

HCID 17810729((1-Naphthyl)methyl)(2-amino-4-methyl-phenyl)amine

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

To (1-naphthyl)methyl)(4-methyl-2-nitro-phenyl)amine (1.0021 g, 3.43 mmol), ethanol (5 ml) and 1,4-dioxane (5 ml) were added, and 2.058 M aqueous sodium hydroxide solution (1 ml) was further added, and refluxed in an oil bath. After 15 minutes, it was removed from the oil bath, and zinc powder (897 mg, 13.72 mmol) was fed thereto in portions. Then it was refluxed again in the oil bath for 2 hours. After 2 hours, it was concentrated under reduced pressure, and dissolved in ethyl acetate (50 ml), and washed twice with saturated saline (25 ml). After drying with magnesium sulfate, it was concentrated under reduced pressure and dried to obtain a brown oil of ((1-naphthyl)methyl)(2-amino-4-methyl-phenyl)amine (943.1 mg).

Workup

  1. temperaturerefluxed in an oil bath
  2. temperatureThen it was refluxed again in the oil bath for 2 hours
  3. waitAfter 2 hours
  4. concentrationit was concentrated under reduced pressure
  5. dissolutiondissolved in ethyl acetate (50 ml)
  6. washwashed twice with saturated saline (25 ml)
  7. dry with materialAfter drying with magnesium sulfate, it
  8. concentrationwas concentrated under reduced pressure
  9. customdried

Sources & evidence

ORD record
ord-d29a8f541a4647cdbb5b42e56acbe54f
Source dataset
uspto-grants-2007_09
Patent number
US07268145B2

Reaction notes

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