2-Nitro-4-phenylmethoxyanisole → 5-(Benzyloxy)-2-methoxyaniline

HRID 1090700Notes

Reaction equation

HRID 1090700 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[O:18][CH3:19])([O-])=O>CO.O=[Pt]=O>[CH3:19][O:18][C:5]1[CH:6]=[CH:7][C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][C:4]=1[NH2:1]

Participants

4

Reactant 1

HCID 156769762-Nitro-4-phenylmethoxyanisole

Product 1

HCID 156769785-(Benzyloxy)-2-methoxyanilineYield 76.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

2-Nitro-4-phenylmethoxy-anisole (73 g) and 1.3 g of platinium oxide in 600 ml of methanol were hydrogenated at room temperature. The catalyst was filtered on Celite and the methanol evaporated. The residue was dissolved in methylene chloride and washed with dilute sodium hydroxide then water. Evaporation of the solvent gave 49.35 g (Yield=76%) of 2-methoxy-5-phenylmethoxy-aniline.

Workup

  1. customwere hydrogenated at room temperature
  2. filtrationThe catalyst was filtered on Celite
  3. customthe methanol evaporated
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washwashed with dilute sodium hydroxide
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-aaf22e84238f44f2845196c296a9e9b4
Source dataset
uspto-grants-1992_01
Patent number
US05082847

Reaction notes

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