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ChemicalBook CAS DataBase List 2-Amino-3,4-dimethyl-3H-imidazo[4,5-f]quinoline
77094-11-2

2-Amino-3,4-dimethyl-3H-imidazo[4,5-f]quinoline synthesis

11synthesis methods
Heterocyclic amines are formed by condensation of creatinine with amino acids during heating or cooking of meat (beef, pork, chicken, and fish). They have also been detected in processed food flavorings, beer, wine, and cigarette smoke. 2-Amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ) and related heterocyclic amines are produced in small quantities for research purposes. Exposure to MeIQ and related heterocyclic amines occurs primarily through the consumption of cooked meats.Concentrations of heterocyclic amines in meats varied under different cooking conditions (375). The highest concentrations of MeIQ were detected in grilled fish, which appear to be the major dietary source of heterocyclic amines in Japanese. U.S. surveys of dietary intakes of heterocyclic amines in cooked foods have also been reported. Occupational exposure to heterocyclic amines may occur by inhalation of aerosolized particles formed during the cooking process.
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Yield:-

Steps:

Multi-step reaction with 7 steps
1: 75 percent / HNO3, conc. H2SO4 / 0.5 h / 0 °C
2: 1.) H2SO4, arsenic acid; 2.) H2 / 2.) 10percent Pd-C / 1.) 130 deg C, 18 h; 2.) EtOH, 7 d
3: 90 percent / (CH3CO)2O / 2 h / Ambient temperature
4: 90 percent / LiAlH4 / tetrahydrofuran / 0 °C
5: 68 percent / HNO3, H2SO4 / 1 h / 0 °C
6: 80 percent / SnCl2, HCl / 1 h / 100 °C
7: ethanol / 2 h

References:

Lee;Hashimoto;Shudo;Okamoto [Chemical and Pharmaceutical Bulletin,1982,vol. 30,# 5,p. 1857 - 1859]