Reaktion #59368

Reaktionsgleichung

Rochelle's salt

2-[(2-bromophenyl)-hydrazono]-N-ethyl-2-cyanoacetamide

aluminum chloride

→

title compound

Ausbeute 69.3%

4-Amino-8-bromo-N-ethyl-cinnoline-3-carboxamide

Ausbeute 69.3%

Lösungsmittel

ethyl acetate

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated
2. 2
   Temperaturcooled
3. 3
   workup.STIRRINGAfter stirring for 30 minutes
4. 4
   Sonstigethe organic layer was decanted into a separator funnel
5. 5
   Waschen(The white precipitate was rinsed with ethyl acetate three times
6. 6
   Waschen) The organic layer was washed with 1:1 brine
7. 7
   TrocknenRochelle's salt solution, dried over sodium sulfate
8. 8
   Einengenconcentrated to a light brown solid
9. 9
   Filtrationfiltered

Vorschrift

To a stirred solution of 2-[(2-bromophenyl)-hydrazono]-N-ethyl-2-cyanoacetamide (260 mg, 0.88 mmol) in anhydrous toluene (10 mL) was added aluminum chloride (370 mg, 2.78 mmol). The reaction was heated with vigorous stirring at 90° C. for 1.5 hours, cooled, diluted with ethyl acetate (40 mL), and treated with Rochelle's salt (saturated aqueous solution). After stirring for 30 minutes, the organic layer was decanted into a separator funnel. (The white precipitate was rinsed with ethyl acetate three times.) The organic layer was washed with 1:1 brine:Rochelle's salt solution, dried over sodium sulfate, and concentrated to a light brown solid. The solid was slurred in ether and filtered to afford the title compound as a brown solid (180 mg, 69%). 1H NMR (300.132 MHz, CDCl3) δ 8.52 (s, 1H), 8.13 (dd, J=7.4, 1.1 Hz, 1H), 7.82 (dd, J=8.4, 1.1 Hz, 1H), 7.51 (dd, J=8.4, 7.5 Hz, 1H), 3.56 (dq, J=5.8, 7.3 Hz, 2H), 1.31 (t, J=7.3 Hz, 3H). MS APCI, m/z=395/397 (M+H). HPLC 1.90 min.

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