HCID 86584083, compound → HCID 21956379, compound
Reaction equation
[C:1](/[C:3](=[CH:8]\[C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH2:18][CH2:19][Cl:20])=[CH:11][C:10]=1[N+:21]([O-])=O)/[C:4]([O:6][CH3:7])=[O:5])#[N:2]>C(O)(=O)C.[Fe]>[NH2:2][C:1]1[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][C:9]2[C:10](=[CH:11][C:12]([O:17][CH2:18][CH2:19][Cl:20])=[C:13]([O:15][CH3:16])[CH:14]=2)[N:21]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To methyl (2E)-2-cyano-3-[4-(2-chloroethoxy)-5-methoxy-2-nitrophenyl]-2-propenoate (19.3 g, 56.6 mmol) in 250 mL of acetic acid is added portionwise 12.0 g (215.0 mmol) of iron. The mixture is heated at reflux for 20 minutes, cooled slightly and filtered washing with ethyl acetate. The filtrate is concentrated in vacuo and water is added to the residue. The resulting yellow solid is collected by filtration washing with water to provide 14.6 g of methyl 2-amino-7-[2-chloroethoxy]-6-methoxy-3-quinolinecarboxylate. An analytical sample is obtained by stirring a portion of the product with a mixture of methanol and aqueous ammonium hydroxide. The undissolved solids are removed by filtration. Upon standing solids appeared in the filtrate and are collected to provide methyl 2-amino-7-[2-chloroethoxy]-6-methoxy-3-quinolinecarboxylate as light yellow crystals, mp 145–157° C.