[CH2:1]([O:11][C:12]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([N+:24]([O-])=O)=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[N:17]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(OCCCC)CCC.C(O)(=O)C>[Fe].O>[NH2:24][C:19]1[CH:20]=[C:21]([O:22][CH3:23])[C:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2A stirred mixture of 4.7 g (0.013 mole) of 5-decoxy-6-methoxy-8-nitroquinoline, 12 g of degreased 40 mesh iron filings, 6 ml of butyl ether, 6 ml of acetic acid and 30 ml of water was heated at 100° for 2 hr, cooled and filtered. The solid was washed with water, dried and extracted with diethyl ether. Evaporation of the diethyl ether, solution of the residue in petroleum ether (20°-40°) and cooling in Dry-Ice acetone gave 3.6 g of pale green solid. Two crystallizations from petroleum ether (20°-40°) (carbon) provided 2.3 g (54%) of amino compound as yellow-green solid, mp 65°.
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