Reaktion #172727

Reaktionsgleichung

oxygen

HCl

t-BuOK

cyanoacetamide

(E)-5-methylhept-3-en-2-one

2

3-(aminomethyl)-6-methyl-4-propyl-2(1H)-pyridinone

t-BuOK

→

title compound

Ausbeute 53.0%

4-sec-butyl-1,2-dihydro-6-methyl-2-oxopyridine-3-carbonitrile

Ausbeute 53.0%

Lösungsmittel

water

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGstirred at RT for 48 h
3. 3
   TemperaturThe reaction mixture was cooled to 0° C.
4. 4
   Sonstigethe resulting reaction mixture
5. 5
   workup.STIRRINGwas stirred for 15 min
6. 6
   FiltrationThe separated solid was collected by filtration
7. 7
   Waschenwashed with water (10 mL), pet ether (100 mL)
8. 8
   Sonstigedried

Vorschrift

To a stirred solution of t-BuOK (8 g, 71.42 mmol) and cyanoacetamide (6.6 g, 78.57 mmol) in DMSO (80 mL) was added (E)-5-methylhept-3-en-2-one, 2 (9 g, 71.42 mmol) under argon atmosphere at room temperature. The reaction mixture was stirred at room temperature for 1 h and then added additional t-BuOK (24 g, 214.28 mmol) was added. Then argon was displaced by oxygen and stirred at RT for 48 h. The reaction mixture was cooled to 0° C., diluted with water (36 mL) followed by 4N HCl (up to pH˜4) and the resulting reaction mixture was stirred for 15 min. The separated solid was collected by filtration, washed with water (10 mL), pet ether (100 mL) and dried to afford the title compound as yellow solid (7 g, 53%). 1H NMR (DMSO-d6, 400 MHz): δ 0.816-0.779 (t, 3H, J=7.6 Hz), 1.178-1.161 (d, 3H, J=6.8 Hz), 1637-1.505 (m, 2H), 2.24 (s, 3H), 2.814-2.760 (m, 1H), 6.239 (s, 1H), 12.324 (bs, 1H); LCMS (ES−) m/z=189.20 (M−H)

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