HCID 21875453, Verbindung → 5-Amino-3-methoxypyridine-2-carbonitrile

HRID 2110472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2110472
[C:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([N+:11]([O-])=O)=[CH:5][N:4]=1)#[N:2]>CCOC(C)=O.CC(O)=O.[Fe]>[NH2:11][C:6]1[CH:7]=[C:8]([O:9][CH3:10])[C:3]([C:1]#[N:2])=[N:4][CH:5]=1

Komponenten

4

Edukt 1

HCID 21875453HCID 21875453, Verbindung

Produkt 1

HCID 218753365-Amino-3-methoxypyridine-2-carbonitrileAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 22609514Ethyl acetate acetateLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

2-Cyano-3-methoxy-5-nitropyridine (1.0 g, 5.6 mmol) was dissolved in 1:1 EtOAc/AcOH (10 mL) and heated to 65° C. Iron powder (1.61 g, 28 mmol, 325 mesh) was added and the mixture stirred for two h. The mixture was filtered though Celite and the filtrate concentrated in vacuo. The residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified by SiO2 Prep-TLC using CH2Cl2 as the eluent to give the compound 762D (0.805 g, 97%) as an off-white solid. HPLC: 100% at 1.31 min(YMC S5 ODS column) eluting with 10-90% aqueous methanol containing 0.2% phosphoric acid over a 4 min gradient monitoring at 220 nm. MS (ES): m/z 149.90 [M+H]+.

Aufarbeitung

  1. filtrationThe mixture was filtered though Celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by SiO2 Prep-TLC

Quellen und Nachweise

ORD-Eintrag
ord-e1a854ecaea64442ae3db4655ae50544
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517904B2

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