Ammonia → 3-(Benzyloxy)-4-methoxyaniline

HRID 19983Notes

Reaction equation

HRID 19983 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([N+:31]([O-])=O)[CH:20]=[CH:21][C:22]=1[O:23][CH2:24]C1C=CC=CC=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N>CO>[CH2:9]([O:16][C:17]1[CH:18]=[C:19]([NH2:31])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24489Sodium DithioniteHCID 127366801,2-Bis(benzyloxy)-4-nitrobenzene

Product 1

HCID 125477223-(Benzyloxy)-4-methoxyanilineYield 61.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium dithionite (2 g) was added to a solution of 3,4-Dibenzyloxy-1-nitro benzene (2.37 gm) in a mixture of methanol (30 ml)/aqueous ammonia (5 ml). After stirring for 12 hrs at room temperature, the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate (75 ml) and water (75 ml). The ethyl acetate layer was washed with water (25 ml), brine solution (25 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Purification by flash chromatography over silica gel eluting with ethyl acetate/hexane (1:1) provided 1.0 g of 1-Benzyloxy-2-methoxy-5-aminobenzene (Yield=47%).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate (75 ml) and water (75 ml)
  3. washThe ethyl acetate layer was washed with water (25 ml), brine solution (25 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography over silica gel eluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-d743163391f74bb3918b3ed78a729397
Source dataset
uspto-grants-2010_06
Patent number
US07745490B2

Reaction notes

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