Methyl 4-ethyl-3-nitrobenzoate → 3-AMino-4-ethyl-benzoic acid Methyl ester

HRID 514438Notes

Reaction equation

HRID 514438 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[N+:13]([O-])=O)[CH3:2]>[Pd].CO>[NH2:13][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:3]=1[CH2:1][CH3:2])[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 21938352Methyl 4-ethyl-3-nitrobenzoate

Product 1

HCID 133999993-AMino-4-ethyl-benzoic acid Methyl esterYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Charged methyl 4-ethyl-3-nitrobenzoate (5.0 g, 23.92 mmol), Pd/C (500 mg) and methanol (50 mL) to a flask, purged with hydrogen and stirred at r.t. overnight. It was then filtered and concentrated to give 4.0 g of the title compound (94%). 1H NMR (400 MHz, CDCl3): δ 1.26 (3H, t, J=7.6 Hz), 2.54 (2H, q, J=7.6 Hz), 3.73 (2H, s), 3.87 (3H, s), 7.12 (1H, d, J=8.0 Hz), 7.35 (1H, s), 7.41 (1H, d, J=7.6 Hz). [M+H] Calc'd for C10H13NO2, 180. Found, 180.

Workup

  1. custompurged with hydrogen
  2. filtrationIt was then filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-674fb4322903454985707d40b28ea244
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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