HCID 23153311, compound → 4-Amino-3-methoxyphenol

HRID 492711Notes

Reaction equation

HRID 492711 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([O:18][CH3:19])[CH:10]=1)C1C=CC=CC=1.[H][H]>O1CCCC1.CO.[C].[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]=1[O:18][CH3:19]

Participants

6

Reactant 2

HCID 23153311HCID 23153311, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 198180564-Amino-3-methoxyphenol

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-Benzyloxy-3-methoxy-4-nitrobenzene (11.0 g) was dissolved in tetrahydrofuran (100 ml)-methanol (100 ml), and then 10% palladium carbon (5.0 g) was added thereto, followed by replacing with hydrogen inside the system and stirring overnight. After replacing with nitrogen inside the system, the reaction mixture was filtered to remove the catalyst, which was washed with tetrahydrofuran, ethyl acetate and methanol in this order. The filtrate was concentrated under a reduced pressure to give a residue, which was dried in vacuum to provide the titled compound (5.88 g, quantitatively) as brown powder.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customto remove the catalyst, which
  3. washwas washed with tetrahydrofuran, ethyl acetate and methanol in this order
  4. concentrationThe filtrate was concentrated under a reduced pressure
  5. customto give a residue, which
  6. customwas dried in vacuum

Sources & evidence

ORD record
ord-ade38147d3174963bf22dc1fde8861ad
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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