[C:1]([C:3]1[N:8]=[C:7]([CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[N:4]=1)#[N:2].Cl>[Pd].CO>[NH2:2][CH2:1][C:3]1[N:8]=[C:7]([CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[N:4]=1A mixture of 4.4 g of the product from Example 8, 0.35 g 10% palladium-on-carbon catalyst, and 1.5 ml of concentrated hydrochloric acid in 70 ml methanol was shaken under an atmosphere of hydrogen at 46 p.s.i. on a Parr Hydrogenation Apparatus. After 31/2 hours, the solution was filtered through a pad of Celite and the filtrate was concentrated in vacuo. The resulting solid was taken up in water and the aqueous layer was washed with several small portions of ether. Adjustment to pH 13 followed by extraction with methylene chloride, drying, and evaporation of the organic layer gave 1.8 g of the title compound as a light yellowish-orange oil.
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