One-pot preparation of 7-hydroxyquinoline

Organic Process Research and Development

Volumn 10, Issue 1, 2006, Pages 149-152

  Cameron, Mark ^a   Hoerrner, R Scott ^a   McNamara, James M ^a   Figus, Margaret ^a   Thomas, Scott ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

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EID: 33344479261     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0501545     Document Type: Article

References (14)

1. Yokoshima, S.; Ueda, T.; Kobayashi, S.; Sato, A.; Kuboyama, T.; Tokuyama, H.; Fukuyama, T. Pure. Appl. Chem. 2003, 75, 29-38.
2. Tokuyama, H.; Sato, M.; Ueda, T.; Fukuyama, T. Heterocycles 2001, 54, 105.
3. Tokuyama, H.; Fukuyama, T. U.S. Patent Application Publication US 2004/0034217 A1.
4. The Occupational Safety and Health Administration (OSHA) legal airborne permissible exposure limit (PEL) is 0.1 ppm averaged over an 8-h work shift, and 0.3 ppm not to be exceeded during any 15-min work period (National Institute for Occupational Safety and Health). For a summary of the hazards associated with acrolein, see: Bretherick's Handbook of Reactive Chemical Hazards, 6th ed.; Urben, P. G., Ed.; Butterworth-Heinemann: Oxford, 1999; Vol. 1, pp 406-407.
5. 2SO) δ 1.00 (6H, t, J = 7.2 Hz), δ 1.06 (6H, t, J = 7.2 Hz), 1.54 (2H, q, J = 6.8 Hz), 1.89 (2H, q, J = 6.8 Hz), 3.32 (3H, s), 3.25-3.55 (10 H, m) 3.83 (2H, t, J = 6.8 Hz), 4.46 (1H, t, J = 5.2 Hz), 4.62 (1H, t, J = 5.2 Hz), 6.54 (1H, t, J = 2.0 Hz), 6.58 (1H, dd, J = 1.6, 8.4 Hz), 6.85 (1H, dd, J = 2.43, 8.4 Hz), 7.20 (1H, t, J = 8.0 Hz) 7.33 (2H, d, J = 8.4 Hz), 7.42 (2H, d, J = 8.4 Hz).
6. Manske, R. H. F.; Kulka, M. Org. React. 1953, 7, 59.
7. 3) δ 1.10 (3H, t, J = 7.2 Hz), 1.53 (2H, q, J = 6.8 Hz), 2.35 (3H, s) 3.33 (2H, m), 3.43-3.48 (4H, m), 4.45 (1H, t, J = 5.5 Hz), 6.38 (1H, dd, J = 1.6, 8.4 Hz), 6.45 (1H, t, J = 2.1 Hz), 6.86 (1H, dd, J = 1.6, 8.0 Hz), 7.08 (1H, t, J = 8.0 Hz), 7.34 (2H, d, J = 8.4 Hz), 7.41 (2H, d, t J = 8.4 Hz), 9.53 (1H, br).
8. Birch, A. J.; Jackson, A. H.; Shannon, P. V. R. J. Chem. Soc., Perkin 1 1974, 2185-2190.
9. Wardani, A.; Lhomme, J. Tetrahedron Lett. 1993, 34, 6411-6414.
10. A small volume of toluene is added prior to pH adjustment to solubilize polymeric material that otherwise adheres to the precipitated 7-hydroxyquinoline (1).
11. HPLC assay against commercial material as standard.
12. 1.7 g of 1 (6%) is lost to the toluene layer.
13. Grosjean, D.; Fung, K. Anal. Chem. 1982, 54, 1221-1224.
14. Koivusami, E.; Haatainen, E.; Root, A. Anal. Chem. 1999, 71, 86-91.