Acetic Acid → 4-Amino-2,6-dimethylpyridine

HRID 1640954

Reaktionsgleichung

Reaktionsgleichung von HRID 1640954
[N+:1]([C:4]1[CH:5]=[C:6]([CH3:12])[N+:7]([O-])=[C:8]([CH3:10])[CH:9]=1)([O-])=O.C.C(O)(=O)C>CO>[NH2:1][C:4]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([CH3:12])[CH:5]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 297MethaneHCID 209452,6-Lutidine, 4-nitro-, 1-oxide

Produkt 1

HCID 770474-Amino-2,6-dimethylpyridineAusbeute 122,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 4-Nitro-2,6-lutidine 1-oxide (21, 5.1 g, 30 mmol), palladized charcoal (10% Pd, 1 g) and acetic acid (2 ml) in methanol (200 ml) is hydrogenated under pressure (40 psi) over 10 hours using a hydrogenation apparatus. The reaction is followed with LC-MS. After filtration, the filtrate is concentrated. The remaining oil is further dried by lyophilization, yielding 4.5 g of 4-amino-2,6-lutidine (22) containing approximately 15% acetic acid. 1H NMR (300 MHz, CDCl3) δ 2.3 (s, 6H), 7.2 (s, 2H). MS, m/z 123 (M+1), 243 (2M−1).

Aufarbeitung

  1. filtrationAfter filtration
  2. concentrationthe filtrate is concentrated
  3. customThe remaining oil is further dried by lyophilization

Quellen und Nachweise

ORD-Eintrag
ord-0662a9a6ac4f4f398796dc9822224437
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08114888B2

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