HYPOPHOSPHOROUS ACID DEAMINATIONS 295 Doubling the amount of hypophosphorous acid does not increase the yield of m-nitrotoluene. 82 It has recently been found that, on using only 0.76 mole of hypophosphorous acid per mole of 3-nitro-4-aminotoluene, a 70% yield of m-nitrotoluene is obtained. 84 Another departure from the above directions consists in permitting the cold reaction mixture to come to room temperature in six hours, after which it is allowed to remain overnight before being worked up. 84 Toluene^ 82 fronK)-Toluidine. In a 1-L flask are placed 21.4 g. (0.2 mole) of o-toluidine, 75 cc. of concentrated hydrochloric acid (sp. gr. 1:19), and 25 cc. of water. The flask is immersed in an ice-salt mixture and is fitted with an efficient stirrer. While a temperature of —5° to 0° is maintained, a solution of 14.5 g. (0.204 mole) of 97% sodium nitrite in 35 cc. of water is slowly added from a dropping funnel. As the reac-' tion proceeds, the mixture becomes more fluid and the nitrite may be
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