[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].N#N.[H-].[Na+].[CH3:22]I>CN(C=O)C.O.CCCCCC.C(OCC)(=O)C>[CH3:22][N:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15]
To a solution of tert-butyl (3-nitrophenyl)carbamate (6.0 g) in DMF (35 mL) in a 100 mL 3-neck RBF equipped with N2 Bubbler and thermo pocket was added NaH (1.21 g) portion wise and stirred 1.0 hr at room temperature. Methyl iodide (5.37 g in 15 mL DMF) was added dropwise to the reaction mixture at 0° C. The mixture was allowed to cool to room temperature and stirred for 2 hr. The reaction was monitored on TLC using hexane:ethyl acetate (9:1) as mobile phase. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine solution, dried over sodium sulfate and concentrated completely under reduce pressure at 40° C. to give 6.0 g of tert-butyl methyl(3-nitrophenyl)carbamate 7. 1H NMR: DMSO-d6 (400 MHz): 1.43 (s, 9H), 3.26 (s, 3H), 7.62 (t, 1H, J=8.4), 7.77 (d, 1H, J=8), 8.00 (d, 1H, J=9.2), 8.18 (s, 1H).
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