HCID 90409179, compound → 2H-1,4-Benzoxazin-5-amine, 3,4-dihydro-3-phenyl-
Reaction equation
[N+:1]([C:4]1[C:9]2[N:10]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][O:13][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>CO>[C:14]1([CH:11]2[NH:10][C:9]3=[C:4]([NH2:1])[CH:5]=[CH:6][CH:7]=[C:8]3[O:13][CH2:12]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
The 5-nitro-3-phenyl-2H-1,4-benzoxazine oil was taken up in MeOH (50 mL) in a Parr shaker bottle, deoxygenated with nitrogen, the catalyst 10% Pd on carbon (0.25 g) was added, the reaction vessel was charged to 55 psi with hydrogen and shaken. After 2 h the reaction was complete by LC/MS. The reaction was filtered to remove the catalyst and concentrated under reduced pressure to give 3-phenyl-3,4-dihydro-2H-1,4-benzoxazin-5-amine as a dark oil. (3.5 g, 97%). LCMS calc. for C14H15N2O (M+H)+: m/z=227.1. found: 227.1. 1H NMR (500 MHz, DMSO-d6) δ 7.44 (d, J=7.4 Hz, 2H), 7.37 (dd, J=7.5 Hz, 2H), 7.31 (t, J=7.2 Hz, 1H), 6.35 (dd, J=7.9 Hz, 1H), 6.21 (dd, J=7.8, 1.0 Hz, 1H), 6.07 (d, J=7.9 Hz, 1H), 5.00 (s, 1H), 4.62 (s, 2H), 4.44 (dd, J=4.9, 2.6 Hz, 1H), 4.21-4.13 (m, 1H), 3.87 (dd, J=10.4, 7.7 Hz, 1H).