Reaktionsgleichung
N[C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][CH:3]=1.N([O-])=O.[K+].[OH-].[Na+].[ClH:21]>O>[Cl:21][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][CH:3]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a precooled (−10° C.) suspension of 6-amino-2-(pivaloylamino)pyridine (28.00 g, 0.145 mol) in conc. aqueous HCl (150 mL) was added potassium nitrite (14.81 g, 0.174 mol) dissolved in water (8 mL) over a 1.5 h period. The resulting reaction mixture was stirred for 5 h at −10° C. under nirogen, before ajustment of the pH to 9 by addition of conc. aqueous NaOH. The aqueous solution was extracted with ethyl acetate (3×100 mL) and the organic fractions washed with 2M NaOH (3×40 mL). The organic phase was dried (MgSO4), evaporated in vacuo and recrystallised from n-hexane/ethyl acetae to give the desired product (17,70 g (58%) as a white powder (m.p. 86-87° C.). 1H NMR (DMSO-d6): δ 10.08 (s br, 1H), 8.04 (d, 8.1 Hz, 1H), 7.81 (t, 8.1 Hz, 1H), 7.17 (d, 8.1 Hz, 1H), 1.22 (s, 9H). 13C NMR (DMSO-d6): δ 177.4, 152.5, 147.8, 141.4, 119.0, 112.8, 39.4, 26.8. FAB+ MS (m/z): 213.06 M+H+, calc. for C10H13ClN2O+H+ 213.0795.
Aufarbeitung
- customThe resulting reaction mixture
- extractionThe aqueous solution was extracted with ethyl acetate (3×100 mL)
- washthe organic fractions washed with 2M NaOH (3×40 mL)
- dry with materialThe organic phase was dried (MgSO4)
- customevaporated in vacuo
- customrecrystallised from n-hexane/ethyl acetae
Quellen und Nachweise
- ORD-Eintrag
- ord-531049e6050f43a7a7b981ebb9448f97
- Quelldatensatz
- uspto-grants-2003_10
- Patentnummer
- US06632919B1
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