反応 #470110

反応方程式

hydrazoic acid

1,4-dichlorophthalazine

triethylamine

→

phthalazine

収率 15.1%

溶媒

xylene

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度at reflux under nitrogen for 20.5 h
3. 3
   その他the solvent evaporated in vacuo
4. 4
   その他the residue partitioned between dichloromethane and water
5. 5
   その他The aqueous was separated
6. 6
   抽出re-extracted with dichloromethane (×2)
7. 7
   乾燥The combined extracts were dried (MgSO4)
8. 8
   その他evaporated in vacuo
9. 9
   その他the residue chromatographed on silica gel eluting with ethyl acetate

実験手順

A mixture of the preceding hydrazoic acid (798 mg, 3.91 mmol), 1,4-dichlorophthalazine (778 mg, 3.91 mmol) and triethylamine (0.54 ml, 3.9 mmol) in xylene (28 ml) was heated at reflux under nitrogen for 20.5 h. The mixture was cooled to room temperature, the solvent evaporated in vacuo and the residue partitioned between dichloromethane and water. The aqueous was separated and re-extracted with dichloromethane (×2). The combined extracts were dried (MgSO4), evaporated in vacuo and the residue chromatographed on silica gel eluting with ethyl acetate, then 5% methanol/dichloromethane to afford the title-phthalazine (77 mg, 6%), 1H NMR (360 MHz, CDCl3/d6-DMSO) δ 7.51 (1H, m, Ar—H), 7.55 (1H, s, Ar—H), 7.99 (1H, m, Ar—H), 8.11 (1H, m, Ar—H), 8.24 (1H, m, Ar—H), 8.38 (1H, d, J=7.8 Hz, Ar—H), 8.78 (1H, m, Ar—H), 8.83 (1H, m, Ar—H), 9.18 (1H, br s, Ar—H); MS (ES+) m/e 349 [MH]+.

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