3-Dimethoxymethyl-4-nitro-benzoic Acid Methyl Ester → 4-Amino-3-dimethoxymethyl-benzoic Acid Methyl Ester

HRID 1788401Notes

Reaction equation

HRID 1788401 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[C:6]([CH:13]([O:16][CH3:17])[O:14][CH3:15])[CH:5]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([CH:13]([O:14][CH3:15])[O:16][CH3:17])[CH:5]=1

Participants

4

Reactant 1

HCID 576030843-Dimethoxymethyl-4-nitro-benzoic Acid Methyl Ester

Product 1

HCID 576031164-Amino-3-dimethoxymethyl-benzoic Acid Methyl Ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

100 mg 10% Pd/C and 1 g Mg2SO4 were suspended in 20 mL methanol and were hydrogenated in a Parr apparatus at 30 psi for 15 minutes. The apparatus was opened, and 1.22 g (4.78 mmol) of Compound 5 dissolved in 40 mL methanol was added, followed by 2 mL TEA. The mixture was hydrogenated at 30 psi for 30 minutes, the catalyst was removed by means of filtration and the solution was evaporated to dryness. The solid material was dried over P2O5/H3PO4 overnight to give Compound 6.

Workup

  1. additionwas added
  2. waitThe mixture was hydrogenated at 30 psi for 30 minutes
  3. customthe catalyst was removed by means of filtration
  4. customthe solution was evaporated to dryness
  5. dry with materialThe solid material was dried over P2O5/H3PO4 overnight

Sources & evidence

ORD record
ord-8abe8252512649bcaa209f9c32202d50
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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