1-[4-(4-Nitrophenoxy)phenyl]ethanone → 1-[4-(4-Aminophenoxy)phenyl]ethan-1-one

HRID 1474639Notes

Reaction equation

HRID 1474639 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 1

HCID 2386041-[4-(4-Nitrophenoxy)phenyl]ethanone

Product 1

HCID 7892361-[4-(4-Aminophenoxy)phenyl]ethan-1-oneYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 1-(4-(4-nitrophenoxy)phenyl)ethanone (9.0 g, 35.02 mmol), in methanol (50 mL) under nitrogen atmosphere, was added a solution of 10% palladium on charcoal (1.80 g, 20% by weight) in methanol (20 mL). The reaction mixture was evacuated and purged with hydrogen balloon and stirred at r.t for 6 h. After the completion of reaction as confirmed by TLC, the reaction mixture was brought under nitrogen atmosphere. The reaction mixture was filtered through celite. The filtrate was concentrated in vacuo to afford the title compound (7.90 g, 99%) as a solid.

Workup

  1. customThe reaction mixture was evacuated
  2. custompurged with hydrogen balloon
  3. customAfter the completion of reaction
  4. filtrationThe reaction mixture was filtered through celite
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-202f8a20930d4b88982a5df8828d8aa5
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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