反応 #44020

反応方程式

compound 104

ethyl 1-(4-chlorophenylsulfonyl)-3-((dimethylamino)methylene)-4-oxo-1,2,3,4-tetrahydropyridine-2-carboxylate

acetic acid

Hydrazine hydrate

→

compound 105

収率 30.4%

ethyl 5-(4-chlorophenylsulfonyl)-4,5-dihydro-1H-pyrazolo[4,3-c]pyridine-4-carboxylate

収率 30.4%

溶媒

EtOH

反応条件

後処理

1. 1
   濃縮The reaction mixture was concentrated in vacuo
2. 2
   洗浄The organic layer was washed with sat. aq. NaHCO3, brine
3. 3
   乾燥dried over Na2SO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated in vacuo
6. 6
   その他to yield crude material that
7. 7
   その他was purified by flash chromatography (50% EtOAc/hexanes)

実験手順

A flask was charged with compound 104 (5.8 g, 14.6 mmol), acetic acid (10 mL) and EtOH (10 mL). Hydrazine hydrate (1.4 mL, 30 mmol) was added and the reaction stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo and the residue was taken up in EtOAc. The organic layer was washed with sat. aq. NaHCO3, brine, dried over Na2SO4, filtered, and concentrated in vacuo to yield crude material that was purified by flash chromatography (50% EtOAc/hexanes) to yield 1.63 g (30%) of compound 105 as a yellow foam. 1H NMR (CDCl3) δ 7.76 (d, J=6.3 Hz, 2H), 7.48-7.41 (m, 3H), 6.90-6.87 (m, 1H), 5.96-5.93 (m, 1H), 5.80 (s, 1H), 4.13-4.11 (m, 2H), 1.24-1.18 (m, 3H; MS (m/z) 368.0 (M+H)+.

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