Ammonia → 3-(Benzyloxy)-4-methoxyaniline

HRID 19988

Reaction equation

HRID 19988 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH2:9]([O:16][C:17]1[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[CH:19][C:18]=1[O:26][CH3:27])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N>CO>[CH2:9]([O:16][C:17]1[CH:22]=[C:21]([NH2:23])[CH:20]=[CH:19][C:18]=1[O:26][CH3:27])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24489Sodium DithioniteHCID 53140362-(Benzyloxy)-1-methoxy-4-nitrobenzene

Product 1

HCID 125477223-(Benzyloxy)-4-methoxyanilineYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium dithionite (1.5 g) was added to a solution of 1-benzyloxy-2-methoxy-5-nitrobenzene (2.5 gm) in a mixture of methanol (20 ml)/aqueous ammonia (4 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 (50 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 0.771 g of 1-Benzyloxy-2-methoxy-5-aminobenzene (Yield=35%).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate (75 ml) and water (50 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-a8453053421e4b9f80ed52c8b94597a9
Source dataset
uspto-grants-2010_06
Patent number
US07745490B2

Linked notes

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