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

HRID 1807261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1807261
[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.[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]

Komponenten

4

Edukt 1

HCID 57426183Methyl 4-cyano-2-methoxybenzoate

Produkt 1

HCID 67094960Methyl 4-(aminomethyl)-2-methoxybenzoateAusbeute 37,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 4-cyano-2-methoxy benzoic acid (1.0 g, 5.65 mmol, Biogene) in methanol was reacted with p-toluenesulfonic acid monohydrate (285.6 mg, 1.479 mmol) and heated to reflux for 16 hrs. The solvent was removed and the reaction residue was extracted with EtOAc, and washed with saturated sodium carbonate, water, and saturated NaCl, and dried over Na2SO4 to give 4-Cyano-2-methoxy-benzoic acid methyl ester (1.04 g, 96%). This ester (1.01 g, 5.28 mmol) in methanol (50 mL) was reacted with Raney Ni (3 spatula tips full, exact amount unknown, Aldrich) under 50 psi H2 in a Parr apparatus for 16 hrs. After filtering through Celite and concentrating, the crude mixture was purified by silica gel chromatography using methanol and methylene chloride to give 4-aminomethyl-2-methoxy-benzoic acid methyl ester (385.7 mg, 37%).

Aufarbeitung

  1. filtrationAfter filtering through Celite
  2. concentrationconcentrating
  3. customthe crude mixture was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1091679f84ff45c5b24764c2a9390693
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354444B2

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