4-(Benzyloxy)-2-nitrophenol → 2-Amino-4-(benzyloxy)phenol

HRID 964861Notes

Reaction equation

HRID 964861 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([N+:16]([O-])=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CN(C)C=O.[Pt]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([NH2:16])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 46066344-(Benzyloxy)-2-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 141698072-Amino-4-(benzyloxy)phenol

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6228DimethylformamideSolvent

Procedure

50 g. 4-benzyloxy-2-nitrophenol [U.S. Pat. No. 4,603,2091] (Compound XXII) is dissolved in 100 mL dimethylformamide to give a yellow solution which is shaken in the presence of 5% platinum on charcoal under 40 psi pressure of hydrogen. After 12 hours, the reduction is colorless and is filtered through diatomaceous earth to remove the catalyst. The clear filtrate is diluted to 800 mL with ethyl acetate and is washed three times with 500 mL water. The organic layer is evaporated to yield a clear oil, which is triturated with cold methanol and filtered to give 4-benzyloxy-2-aminophenol as a gray solid (Compound XXIII).

Workup

  1. customto give a yellow solution which
  2. filtrationis filtered through diatomaceous earth
  3. customto remove the catalyst
  4. additionThe clear filtrate is diluted to 800 mL with ethyl acetate
  5. washis washed three times with 500 mL water
  6. customThe organic layer is evaporated
  7. customto yield a clear oil, which
  8. customis triturated with cold methanol
  9. filtrationfiltered

Sources & evidence

ORD record
ord-263cde07c9db44b095470cd0fe464540
Source dataset
uspto-grants-1998_06
Patent number
US05773227

Reaction notes

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