Uses
4-Methoxy-1-indanone is suitable for use in the comparative study of the effect of different substituents on various benzo-fused ketones on the reaction kinetics by studying the biocatalysed oxidation reaction.
It may be used in the following studies:
- Synthesis of isomeric mixture of oximes.
- As a starting material in the synthesis of benzo-fused indolizidine and 4-methoxy-1-indanyl compound.
- Synthesis of 4-methoxy-5-nitro-1-indanone by nitration reaction.
- As one of the reactant in the synthesis of E-2-chloro-8-methyl-3-[(4′-methoxy-1′-indanoyl)-2′-methyliden]-quinoline (IQ), a quinoline derivative.
Synthesis
The reaction was carried out with 4-hydroxy-1-indanone (125 mg) and iodomethane (263 μL) in the presence of potassium carbonate (350 mg) in N,N-dimethylformamide (DMF, 4 mL) for 3 h at 50 °C with stirring. After completion of the reaction, the mixture was poured into 1N hydrochloric acid (20 mL) and extracted with ether (4 × 10 mL). The organic layers were combined, dried with anhydrous magnesium sulfate, filtered and concentrated to give 4-methoxy-1-indanone intermediate as a clear oil (131 mg, 96% yield). Mass spectral analysis showed [MH]+ = 163.
References
[1] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 9, p. 1756 - 1759
[2] Patent: US2006/173183, 2006, A1. Location in patent: Page/Page column 114
[3] European Journal of Medicinal Chemistry, 2013, vol. 69, p. 920 - 930
[4] Patent: WO2014/19344, 2014, A1. Location in patent: Paragraph 00821
[5] Patent: WO2014/82380, 2014, A1. Location in patent: Paragraph 00314; 00316
