Ethyl (3-nitrophenyl)acetate → Ethyl 2-(3-aminophenyl)acetate

HRID 1858238Notes

Reaction equation

HRID 1858238 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 14997011Ethyl (3-nitrophenyl)acetate

Product 1

HCID 13042040Ethyl 2-(3-aminophenyl)acetateYield 105.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 10.3 g (49 mmol) of ethyl 3-nitrophenylacetate in 120 ml of ethanol was hydrogenated over 1 g of 10% palladium on charcoal for 6 hours. The mixture was filtered and the filtrate evaporated to give 9.3 g (100%) of ethyl 3-aminophenylacetate as a yellow oil. [NMR spectrum (250 MHz) δ1.19(t) (3H), δ3.48(s) (2H), δ4.16(q) (2H), δ7.48(dd) (1H), δ7.62(d) (1H), δ8.12(m) (2H)].

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-cfcfaf5454d44793b670c2c555e4cd33
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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