Organic Lab Reactions 286

Organic Lab Reactions 286 - REDUCTION WITH HYPOPHOSPEOROUS...

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REDUCTION WITH HYPOPHOSPEOROUS ACID 28X The yields obtained on deaminating the following amines further illus- trate the wide utility "of hypophosphorous acid: 2,4-diethyl-6-bromoaniline (70%), 89 3-nitro-4-aminophenylarsonic acid (45%), 90 3-amino-6-bromo- benzoic acid (75%), 13 3,3'-dimethylbenzidine (76-82%), 80 - 81 4-amino-7- chlorohydrindone-1 (85%), 91 5-methyl-8-aminoquinoline (72%) M o-(J3- phenylethyl)-aniline (XXII) (47%). M In the last case, when ethanol is used dibenzyl is not obtained; instead the products are 9,10-dihydro- phenanthrene (ca. 50%) and o-(|3-phenylethyl)-phenol (23%). M CH 2 —CH 2 xxn This is not the only instance where hypophosphorous acid is more effec- tive than ethyl alcohol. For example, whereas deamination of o-toluidine by the hypophosphorous acid procedure affords toluene in 70-75% yield, 82 treatment with ethanol gives o-ethoxytoluene in approximately 50% yield. 10
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This note was uploaded on 11/20/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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