Methyl 2-(2-methyl-5-nitrophenyl)acetate → Methyl 2-(5-amino-2-methylphenyl)acetate

HRID 424704Notes

Reaction equation

HRID 424704 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:6]=1[CH3:14]>C(O)C.[Pd]>[NH2:11][C:9]1[CH:8]=[CH:7][C:6]([CH3:14])=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:15])[CH:10]=1

Participants

4

Reactant 1

HCID 46738291Methyl 2-(2-methyl-5-nitrophenyl)acetate

Product 1

HCID 46741401Methyl 2-(5-amino-2-methylphenyl)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(2-Methyl-5-nitrophenyl)acetic acid methyl ester 14 (32 g, 153 mmol) is dissolved in ethanol (750 mL). To this solution is added 10% palladium on carbon (3.2 g). After purging the reaction flask of oxygen, a balloon filled with hydrogen is fitted. The reaction is stirred at rt for 16 h. After removing the catalyst by filtering through a celite plug and removing the solvent in vacuo, the crude product is purified using flash chromatography (ethyl acetate:petroleum ether=5:1). The product 7 is isolated as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 6.9 (d, J=7.8 Hz), 6.59 (m, 1H), 6.56 (m, 1H), 3.69 (s, 3H).

Workup

  1. customAfter purging the reaction flask of oxygen
  2. additiona balloon filled with hydrogen
  3. customis fitted
  4. customAfter removing the catalyst
  5. filtrationby filtering through a celite plug
  6. customremoving the solvent in vacuo
  7. customthe crude product is purified

Sources & evidence

ORD record
ord-c8b26c25b8aa48218edc872052a4b321
Source dataset
uspto-grants-2012_01
Patent number
US08106068B2

Reaction notes

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