[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([N+:12]([O-])=O)[C:5]([C:15]2[CH:19]=[CH:18][O:17][C:16]=2[CH:20]=O)=[CH:4][CH:3]=1.CO.N>Cl.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2]>[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]2[C:5]([C:15]3[CH:19]=[CH:18][O:17][C:16]=3[CH:20]=[N:12]2)=[CH:4][CH:3]=1
1M Hydrochloric acid (14 drops) was added to a solution of iron (II) sulfate heptahydrate (18.44 g) in water (50 mL) and the resultant solution was added to methyl 6-amino-3-(2-formylfuran-3-yl)-2-nitrobenzoate (Intermediate 30, 2.02 g). The resultant mixture was stirred and heated at reflux for 10 minutes then cooled to 70° C. Methanol (50 mL) was added followed by aqueous ammonia (33%, 19.2 mL) and the mixture was stirred and heated at reflux for 5 hours. After cooling, methanol (50 mL) was added and the mixture was filtered through Celite and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a DMAW 350 followed by DMAW 240 and DMAW 120 to give methyl 7-aminofuro[2,3-c]quinoline-6-carboxylate (0.27 g) as a brown solid.
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