A practical, kilogram-scale implementation of the Wolff-Kishner reduction

Organic Process Research and Development

Volumn 13, Issue 3, 2009, Pages 576-580

  Kuethe, Jeffrey T ^a   Childers, Karla G ^a   Peng, Zhihui ^a   Journet, Michel ^a   Humphrey, Guy R ^a   Vickery, Thomas ^a   Bachert, Donald ^a   Lam, Thientu T ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

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[No Author keywords available]

Indexed keywords

EID: 66249136328     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op9000274     Document Type: Article

References (59)

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48. Hydrazine concentrations were monitored by a combination of methods found in Jogota, N. K.; Chetram, A. J.; Nair, J. B. J. Pharm. Biomed. Anal. 1998, 16, 1083 and Larson, S.L.; Strong, A. B. Ion Chromatography with Electrochemical Detection for Hydrazine Quantitation in Enviornmental Samples Technical Report IRRP-96-3, March 1996. See Experimental Section for exact method employed.
49. Safeskin Purple Nitrile Xtra Exam Gloves, available from Fisher Scientific and impervious to hydrazine, were employed in all operations.
50. A flammable atmosphere would be one containing ?38 mol % hydrazine.
51. The DSC runs were conducted on TA Instruments 2920 DSC cells operating under TA Instruments' Thermal Advantage software, ver. 1.1 A. A reusable pressure-tight cell made of either Hastelloy B-2 or tantalum-lined Hastelloy B-2 was used.
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55. A glass vessel was employed. Etching was significant after three consecutive runs in the same flask.
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58. For an alternative waste disposal procedure, see ref 10.
59. The filtrate containing aqueous hydrazine waste was disposed of by careful dilution with commercial bleach and sent for disposal to an outside vendor.