2-Methoxy-4-nitrophenol acetate → HCID 22646533, compound

HRID 1009803Notes

Reaction equation

HRID 1009803 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[O:14][CH3:15])(=[O:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[O:14][CH3:15])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 499852-Methoxy-4-nitrophenol acetate

Product 1

HCID 22646533HCID 22646533, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the 2-methoxy-4-nitrophenyl acetate prepared in Part A (99.2 mg, 0.47 mmol) in EtOAc (4.5 mL) was added palladium on carbon (33.0 mg, 5% dry basis, Degussa type: 50% water content). The suspension was hydrogenated (1 atm, balloon) for 3 h, filtered through CELITE® and the filter cake was rinsed with MeOH (5×10 mL). Evaporation of the combined filtrates gave the desired aniline (84.8 mg, quant.) as a brown oil: MS (electrospray, + ions) m/z 182 (M+H).

Workup

  1. customfor 3 h
  2. filtrationfiltered through CELITE®
  3. washthe filter cake was rinsed with MeOH (5×10 mL)
  4. customEvaporation of the combined filtrates

Sources & evidence

ORD record
ord-a9f28f08a5034bafafe25bda7546d844
Source dataset
uspto-grants-2011_07
Patent number
US07973159B2

Reaction notes

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