2,2,4-trimethyl-6-nitro-2H-1,4-benzoxazin-3(4H)-one → 6-amino-2,2,4-trimethyl-2H-1,4-benzoxazine-3(4H)-one
Reaction equation
[CH3:1][C:2]1([CH3:17])[C:7](=[O:8])[N:6]([CH3:9])[C:5]2[CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=[CH:13][C:4]=2[O:3]1>CO.[Pd]>[NH2:14][C:11]1[CH:12]=[CH:13][C:4]2[O:3][C:2]([CH3:1])([CH3:17])[C:7](=[O:8])[N:6]([CH3:9])[C:5]=2[CH:10]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 2,2,4-trimethyl-6-nitro-2H-1,4-benzoxazin-3(4H)-one (290 mg, 1.23 mmol, 1 equiv.) in 10 mL of MeOH in the presence of 29 mg of Pd/C was hydrogenated at room temperature for 3 h. The reaction mixture was then filtered through a pad of celite and the filtrate was concentrated to give 240 mg (Yield=95%) of product as a pale brown solid which was used in the next step without further purification.