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

HRID 2263654Notes

Reaction equation

HRID 2263654 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-dd6727beecb141a8900f82127459fd74
Source dataset
uspto-grants-2010_12
Patent number
US07851622B2

Reaction notes

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