5-Methoxy-2-nitrophenol → 2-Amino-5-methoxyphenol

HRID 512440Notes

Reaction equation

HRID 512440 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:10]([O-])=O)=[C:7]([OH:9])[CH:8]=1>[Pd].C(OCC)(=O)C.C(O)C>[NH2:10][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][C:7]=1[OH:9]

Participants

4

Reactant 1

HCID 2196355-Methoxy-2-nitrophenol

Product 1

HCID 99421632-Amino-5-methoxyphenolYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

Subsequently, a mixture of 5-methoxy-2-nitrophenol (7.47 g) and 10% Pd/C (1.87 g) was prepared in an ethyl acetate/ethanol (100 mL, 1:1 v/v) mixture. The resulting slurry was stirred under an H2 atmosphere for 3.5 h at room temperature. Hydrogen was subsequently purged from the reaction flask and the reaction mixture was filtered through Celite. After washing the celite pad with additional solvent, volatiles in the resultant filtrate were removed in vacuo to give 2-amino-5-methoxyphenol (6.03 g, 98%).

Workup

  1. customHydrogen was subsequently purged from the reaction flask
  2. filtrationthe reaction mixture was filtered through Celite
  3. washAfter washing the celite pad with additional solvent, volatiles in the resultant filtrate
  4. customwere removed in vacuo

Sources & evidence

ORD record
ord-851915fcb78d4557adf270c774724a48
Source dataset
uspto-grants-2015_08
Patent number
US09102636B2

Reaction notes

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