1H-indole-2,3-dione 3-[(4-nitrophenyl)hydrazone] synthesis
- Product Name:1H-indole-2,3-dione 3-[(4-nitrophenyl)hydrazone]
- CAS Number:31107-06-9
- Molecular formula:C14H10N4O3
- Molecular Weight:282.25
Yield:31107-06-9 92%
Reaction Conditions:
in N,N-dimethyl-formamide at 20;
Steps:
4.2. Preparation of compounds 2a-2j
General procedure: A mixture of isatin (1.4722 g,10.0 mmol), ethyl bromide (1.0905 g,10.0 mmol) and anhydrous K2CO3 (2.0 g,14.5 mmol) in DMF (10 mL) was stirred vigorously for 12 h at room temperature and complete reaction was detected by TLC analysis. The reaction mixture was poured into water (100 mL) and the precipitate was concentrated to give crude product 1a and recrystallized from EtOH.21 A mixture of 1a (0.8755 g, 5.0 mmol), phenylhydrazine hydrochloride (0.7325 g,5.0 mmol) in DMF (10 mL) was stirred vigorously at room temperature overnight. The reaction mixture was poured into water (100 mL) and extracted with ethyl acetate (320 mL). The combined organic layer was dried with MgSO4 and the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography eluting (silica gel, ethyl acetate/petroleum ether1:5) leading to phenylhydrazone derivative 2d as a yellow solid.22
References:
Zheng, Jie;Li, Yujin;Cui, Yanhong;Jia, Jianhong;Ye, Qing;Han, Liang;Gao, Jianrong [Tetrahedron,2015,vol. 71,# 23,p. 3802 - 3809]
