Ethyl Acetate → 1,9-Diaminoacridine
Reaction equation
[N+:1]([C:4]1[C:17]2[C:8](=[N:9][C:10]3[C:15]([C:16]=2[NH2:18])=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:7]=[CH:6][CH:5]=1)([O-])=O.C(OCC)(=O)C.C([O-])=O.[NH4+]>CO>[NH2:1][C:4]1[C:17]2[C:8](=[N:9][C:10]3[C:15]([C:16]=2[NH2:18])=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:7]=[CH:6][CH:5]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a 50 mL rbf equipped with a nitrogen bubbler were charged 1-nitro-9-aminoacridine (162 mg, 0.68 mmol) and ethyl acetate (3.4 mL). Methanol (1.7 mL) and Pd/Alumina 10% (22 mg) were added and the reaction mixture was stirred to a fine suspension. Ammonium formate (85 mg, 1.35 mmol) was added and the mixture was stirred for 20 min at room temperature. A further portion of ammonium formate (128 mg, 2.03 mmol) was then added. Stirring was maintained overnight. The reaction mixture was filtered to remove catalyst and concentrated to dryness. The residue was purified by flashmaster column eluting with a gradient elution (DCM→DCM:MeOH 98:2) to afford pure 1,9-diaminoacridine as a brown-yellow solid (57 mg, 40%). 1H NMR and LCMS analyses conformed to structure.