CN(C)[CH:3]=[C:4]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=1[N+:20]([O-])=O)[CH:5]=[C:6]1[C:10](=[O:11])[O:9][C:8]([CH3:12])=[N:7]1.C(OC(=O)C)(=O)C.[H][H]>[Pt].C(O)(=O)C>[CH3:19][C:16]1[CH:15]=[C:14]2[C:13]([C:4](/[CH:5]=[C:6]3\[N:7]=[C:8]([CH3:12])[O:9][C:10]\3=[O:11])=[CH:3][NH:20]2)=[CH:18][CH:17]=1A 500-ml. Parr bottle was charged with 3.17 g. (10 mmol) of 4-[3-dimethylamino-2-(4-methyl-2-nitrophenyl)-2-propen-1-ylidene]-2-methyl-2-oxazolin-5-one, 5 ml. of acetic anhydride, 95 ml. of glacial acetic acid, and 600 mg. of 10% platinum on charcoal, and was shaken under 3 atmospheres of hydrogen for 12 hours. During this time, 34 mmol of hydrogen were absorbed. The reaction was treated as in Example 4. 0.83 g. (35%) of (Z)-4-(6-methylindol-3-ylmethylene)-2-methyl-2-oxazolin-5-one (mp 194°-196° C.) was thereby obtained.
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