HCID 19858077, compound → HCID 19858079, compound
Reaction equation
[CH3:1][C:2]1([CH3:25])[C:6](=[O:7])[O:5][C:4]2[CH:8]=[CH:9][C:10]3[C:15]([C:3]1=2)=[CH:14][C:13]([CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)=[C:12]([N+:22]([O-])=O)[CH:11]=3>[Pd].C(O)(=O)C>[NH2:22][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][C:13]=1[CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)[C:3]1[C:2]([CH3:1])([CH3:25])[C:6](=[O:7])[O:5][C:4]=1[CH:8]=[CH:9]2Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 1,1-dimethyl-7-nitro-8-(1H-1,2,4-triazol-1-ylmethyl)-2(1H)-naphtho[2,1-b]furanone (0.035 g), glacial acetic acid (2 ml) and 10% palladium-on-carbon (0.01 g) was stirred under an atmosphere of hydrogen at room temperature and atmospheric pressure for 2 h. The mixture was filtered, the filtrate was evaporated to dryness under reduced pressure, and the residue was partitioned between ethyl acetate and equeous sodium hydrogen carbonate solution. The ethyl acetate phase was dried and evaporated to dryness under reduced pressure, and the residue was purified by flash chromatography using methanol:ethyl acetate, 1:99 v/v. as eluant, to give 7-amino-1,1-dimethyl-8-(1H-1,2,4-triazol-1-ylmethyl)-2(1H)-naphtho[2,1-b]furanone, m.p. 160°-163°.