5-(Benzyloxy)-1,3-dimethyl-2-nitrobenzene → 4-Benzyloxy-2,6-dimethylaniline

HRID 1284957Notes

Reaction equation

HRID 1284957 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH3:19])[C:12]([N+:16]([O-])=O)=[C:13]([CH3:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([NH2:16])=[C:11]([CH3:19])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 133699565-(Benzyloxy)-1,3-dimethyl-2-nitrobenzene

Product 1

HCID 133699574-Benzyloxy-2,6-dimethylanilineYield 90.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc dust is added to a solution of 5-benzyloxy-2-nitro-m-xylene (22.9g) in 250 ml of glacial acetic acid. The reaction mixture is stirred until the solution is colorless. The reaction mixture is cooled, filtered through Celite to remove excess zinc and the filtrate diluted with H2O and cooled with ice. NH3 is added to make the solution slightly alkaline followed by small amount of sodium hydrosulfite. The product is filtered, dissolved in methylene chloride, dried and concentrated to give 18.3 grams of a tan solid.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered through Celite
  3. customto remove excess zinc
  4. additionthe filtrate diluted with H2O
  5. temperaturecooled with ice
  6. additionNH3 is added
  7. filtrationThe product is filtered
  8. dissolutiondissolved in methylene chloride
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-431db192f8f04f15801da8f69eccf54b
Source dataset
uspto-grants-1986_01
Patent number
US04564640

Reaction notes

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