A novel iodide-catalyzed reduction of nitroarenes and aryl ketones with H 3PO 2 or H 3PO 3: Its application to the synthesis of a potential anticancer agent

Organic Letters

Volumn 13, Issue 19, 2011, Pages 5220-5223

  Wu, George G ^a   Chen, Frank X ^a   LaFrance, Danny ^a   Liu, Zhijian ^a   Greene, Scott G ^a   Wong, Yee Shing ^a   Xie, Ji ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; AROMATIC HYDROCARBON; IODIDE; KETONE; PHOSPHINIC ACID DERIVATIVE; PHOSPHORIC ACID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CATALYSIS; HYDROCARBONS, AROMATIC; IODIDES; KETONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHOSPHINIC ACIDS; PHOSPHORIC ACIDS;

EID: 80054730127     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102174w     Document Type: Article

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23. 3 (0.55 mol), 250mL of hydrobromic acid (48%), and 50 mL of water. The resulting suspension was heated to about 115 °C and stirred at this temperature for 4 h. The reaction mixture was cooled to 60 °C, and 40 mL (0.30 mol) of 50% H3PO2 were added. The reaction mixture was heated to 115 °C for another 6 h. After cooling to 20 °C, the reaction mixture was transferred into a solution of 200 mL of ammonium hydroxide and 100 mL of MeOH. The pH was adjusted to 5 with ammonium hydroxide, and the resulting suspension was stirred for 1 h. The solid was filtered, washed with water, and dried at 60 °C to give 46.9 g (99% yield) of 2 as a mixture of 7- and 9-amino isomers.