Methyl 2-hydroxy-3-nitrobenzoate → Methyl 3-amino-2-hydroxybenzoate

HRID 2415790Notes

Reaction equation

HRID 2415790 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[C:5](=[C:7]([N+:11]([O-])=O)[CH:8]=[CH:9][CH:10]=1)[OH:6]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[C:5](=[C:7]([NH2:11])[CH:8]=[CH:9][CH:10]=1)[OH:6]

Participants

4

Reactant 1

HCID 596904Methyl 2-hydroxy-3-nitrobenzoate

Product 1

HCID 12782444Methyl 3-amino-2-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl-3-nitrosalicylat (4.93 grams, 25 mmol) dissolved in 50 mL of methanol was placed in a Parr bottle together with 200 mg of 10% Pd/C and hydrogenated at room temperature at 45 psi for 2 hours. The reaction was then filtered through celite, concentrated to dryness and the product dried in vacuo. Yield 4.17 gram (99% light green needles, M+168, single spot on TLC.

Workup

  1. filtrationThe reaction was then filtered through celite,
  2. concentrationconcentrated to dryness
  3. customthe product dried in vacuo

Sources & evidence

ORD record
ord-43b6c63c986d4a4fa086348a1be70924
Source dataset
uspto-grants-2004_11
Patent number
US06821977B2

Reaction notes

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