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

HRID 909105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 909105
[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]

Komponenten

5

Edukt 1

HCID 57426183Methyl 4-cyano-2-methoxybenzoate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4a6147c96f02477a9904aa5a14830e57
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017607B2

Notizen zur Reaktion

Wird geladen…