Methyl 3-(hydroxymethyl)-5-nitrobenzoate → Methyl 3-amino-5-(hydroxymethyl)benzoate

HRID 391434Notes

Reaction equation

HRID 391434 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:13]([O-])=O)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]>CO.[Pd]>[NH2:13][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([CH2:2][OH:1])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 10703703Methyl 3-(hydroxymethyl)-5-nitrobenzoate

Product 1

HCID 10535399Methyl 3-amino-5-(hydroxymethyl)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 3-(hydroxymethyl)-5-nitrobenzoate (11.2 g, 53 mmol) in methanol (50 mL) was flushed with nitrogen, and treated with palladium (10% on charcoal, 1.1 g). The flask was flushed with hydrogen and allowed to stir under an atmosphere of hydrogen overnight. The reaction was flushed with nitrogen, filtered through celite, and concentrated. Column chromatography on silica gel (50% ethyl acetate/hexanes) afforded 2.8 g (29%). 1H-NMR (CD3OD, 300 MHz) δ 7.34 (s, 1H), 7.27 (s, 1H), 6.94 (s, 1H), 4.55 (s, 2H), 3.88 (s, 3H). Mass spec.: 182.09 (MH)+.

Workup

  1. customThe flask was flushed with hydrogen
  2. customThe reaction was flushed with nitrogen
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. customColumn chromatography on silica gel (50% ethyl acetate/hexanes) afforded 2.8 g (29%)

Sources & evidence

ORD record
ord-6ea0a676b3d94235a0e1f9d2b6cf77b6
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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