[CH3:1][O:2][C:3]1[C:4]([O:27][CH3:28])=[CH:5][C:6]2[C@H:15]3[C@H:10]([CH2:11][CH2:12][N:13]([CH3:16])[CH2:14]3)[N:9]=[C:8]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)[C:7]=2[CH:26]=1.Cl.[OH-].[Na+]>C(O)C.O.[Fe]>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:8]2[C:7]3[CH:26]=[C:3]([O:2][CH3:1])[C:4]([O:27][CH3:28])=[CH:5][C:6]=3[C@H:15]3[C@H:10]([CH2:11][CH2:12][N:13]([CH3:16])[CH2:14]3)[N:9]=2)=[CH:18][CH:19]=12,7 g of iron turnings are added to a hot solution of 2.0 g of cis-1,2,3,4,4a,10b-hexahydro-8,9-dimethoxy-2-methyl-6-(4-nitrophenyl)-benzo[c][1,6]naphthyridine in 40 cc of ethanol and 13 cc of water. A mixture of 13 cc of ethanol, 3 cc of water and 0.7 cc of 2 N hydrochloric acid is added dropwise within 40 minutes while heating, and the reaction mixture is boiled under reflux for a further 3 hours. 1 cc of a 2 N caustic soda solution is then added, filtration is effected and the filtrate is concentrated by evaporation in a vacuum. The residue is dissolved in chloroform, the solution is dried over sodium sulphate, filtered and concentrated by evaporation in a vacuum. The residue is crystallized from ethyl acetate, whereby yellowish prisms having a M.P. of 168°-170°, are obtained.
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