Ethyl 2-methyl-5-nitrobenzoate → HCID 18690998, compound

HRID 1640010Notes

Reaction equation

HRID 1640010 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]>C(O)C.[Pd]>[NH2:13][C:10]1[CH:11]=[CH:12][C:2]([CH3:1])=[C:3]([CH:9]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 1

HCID 18510875Ethyl 2-methyl-5-nitrobenzoate

Product 1

HCID 18690998HCID 18690998, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-methyl-5-nitrobenzoate (11.5 g, 54 mmol) and 10% Pd/C (1.2 g) in ethanol (200 mL) was shaken under an atmosphere of hydrogen at 40 psi for 18 h. After this time, the mixture was filtered through diatomaceous earth and concentrated under reduced pressure to provide ethyl 5-amino-2-methylbenzoate (9.77 g, 98%) as an off-white solid: 1H NMR (300 MHz, CDCl3) δ 7.25 (d, J=2.6 Hz, 1H), 7.02 (d, J=8.1 Hz, 1H), 6.74 (d, J=8.1 Hz, 1H), 4.33 (q, J=7.2 Hz, 2H), 2.46 (s, 3H), 1.38 (t, J=7.1 Hz, 3H).

Workup

  1. filtrationAfter this time, the mixture was filtered through diatomaceous earth
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9c36d299c9b44339b779d02427b7699a
Source dataset
uspto-grants-2012_02
Patent number
US08110681B2

Reaction notes

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