[H][H].[CH3:3][N:4]([CH2:11][CH:12]([OH:17])[CH2:13][N:14]=[N+]=[N-])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>[Pd].C(O)C>[CH3:3][N:4]([CH2:11][CH:12]([OH:17])[CH2:13][NH2:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1Hydrogen was introduced into a mixture of 1.85 g of 3-(N-methyl-N-phenylamino)-2-hydroxypropylazide (prepared as described in Preparation 89), 0.9 g of 10% w/w palladium-on-carbon and 30 ml of ethanol for 1.5 hours. At the end of this time, the atmosphere was replaced with nitrogen, the palladium-on-carbon catalyst was removed from the reaction mixture by filtration, and the filtrate was concentrated by evaporation under reduced pressure, to give 1.6 g of the title compound which decomposed at 136° C.
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