Methyl 4-cyano-2-methoxybenzoate → Methyl 4-(aminomethyl)-2-methoxybenzoate

HRID 909105Notes

Reaction equation

HRID 909105 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][C:5]=1[O:12][CH3:13]>CO.O.[Ni]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH2:11])=[CH:6][C:5]=1[O:12][CH3:13]

Participants

5

Reactant 1

HCID 57426183Methyl 4-cyano-2-methoxybenzoate

Product 1

HCID 67094960Methyl 4-(aminomethyl)-2-methoxybenzoateYield 37.4%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-cyano-2-methoxy-benzoic acid methyl ester (1.01 g, 5.28 mmol) in methanol (50 mL) was added to Raney-nickel 2800 slurry in water (a few grams washed with methanol to remove the water, Aldrich) and it was put under a 50 psi hydrogen atmosphere for 16 hrs. The mixture was filtered through Celite under an argon atmosphere and concentrated and then purified by flash chromatography to give 4-aminomethyl-2-methoxy-benzoic acid methyl ester (385.7 mg, 34.7%).

Workup

  1. washwashed with methanol
  2. customto remove the water, Aldrich) and it
  3. filtrationThe mixture was filtered through Celite under an argon atmosphere
  4. concentrationconcentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-4a6147c96f02477a9904aa5a14830e57
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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