Methyl 3-nitrobenzoate → Benzoic acid, 3-amino-, methyl ester

HRID 744726

Reaction equation

HRID 744726 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])([O-])=O>C(O)C.O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 69260Methyl 3-nitrobenzoate

Product 1

HCID 78274Benzoic acid, 3-amino-, methyl esterYield 97,246.297%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A mixture of methyl 3-nitrobenzoate (18.1 g, 0.10 mmol) in ethanol/tetrahydrofuran (9:1) and 1.8 g of 10% Pd/C was hydrogenated under a hydrogen atmosphere at atmospheric pressure and ambient temperature for 24 hr. The reaction mixture was filtered through Celite (Celite is a registered trademark of the John-Manville Product Corporation for diatomaceous earth) and washed with ethanol. The solvent was removed in vacuo to give the title compound as a pale yellow solid (14.7 g; 97% yield) which was used without further purification in the next reaction. 1H-NMR (200 MHz; CDCl3) δ7.43 (d, 1H, J=7.6 Hz), 7.35 (t, 1H, J=2.3 Hz), 7.25 (d, 1H, J=2.3 Hz), 7.19 (d, 1H, J=7.7 Hz), 3.89 (s, 3H), 3.7 (bs, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite (Celite
  2. washwashed with ethanol
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a71f7c4bddc342b392fefbd9da060fd6
Source dataset
uspto-grants-1996_09
Patent number
US05559150

Linked notes

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