7H-Indeno[2,1-c]quinolin-7-one, 6-chloro-3-methoxy- synthesis
- Product Name:7H-Indeno[2,1-c]quinolin-7-one, 6-chloro-3-methoxy-
- CAS Number:174635-04-2
- Molecular formula:C17H10ClNO2
- Molecular Weight:295.72
Yield:174635-04-2 78.4%
Reaction Conditions:
in chloroform;water;N,N-dimethyl-formamide;
Steps:
Synthesis of 6-chloro-3-methoxy-7H-indeno[2,1-c]quinoline-7-on
Synthesis of 6-chloro-3-methoxy-7H-indeno[2,1-c]quinoline-7-on A mixture of 3-methoxy-5H-indeno[2,1-c]quinoline-6,7-dion (550 mg, 2.0 mmol) obtained in reference example 8 and phophorous oxychloride (20 ml, 214 mmol) was refluxed with heat in the presence of catalytic amount of N,N-dimethylformamide for 4 hours. The reaction mixture was distilled to dryness. To the residue was added water to obtain a crystal precipitated by filtration. The crystal obtained was dissolved in chloroform to filter off undissolved substances. Recrystallization from benzene gave 460 mg (yield 78.4%) of the title compound. m.p.: 261°-266° C. 1 H-NMR(CDCl3) δ: 8.39(1H, d, J=9 Hz), 8.11(1H, d, J=8 Hz), 7.81(1H, m), 7.64(1H, d-d-d, J=8,8,1 Hz), 7.53(1H, m), 7.41(1H, d, J=2 Hz), 7.33(1H, d-d, J=9,2 Hz), 4.00(3H, s). IR(KBr)cm-1: 1706, 1618, 1564, 1496, 1474, 1464, 1428, 1208, 1186, 1157, 1122, 1060, 1012.
References:
US5710162,1998,A
174635-03-1
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174635-04-2
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