2-AMINO-4-BROMOBENZONITRILE

To a cold solution of oxime 11 (8 g, 33.19 mmol) inCH2Cl2 (200 mL) at 0 °C was added 2, 6-lutidine (4.5 mL, 38.8 mmol) followed by the dropwise addition of triflouromethanesulfonic anhydride (5.6 mL, 33.34 mmol). The cooling bath was removed and the mixture was heated toreflux for 3 h. The reaction mixture was cooled to room temperature and DBU (9.9 mL, 66.3 mmol) was added dropwis ewhile maintaining the internal temperature of the reaction below 30 °C. The mixture was further stirred at room temperature for 1 h and poured with vigorous stirring into excess dilute NaHCO3. This mixture was then stirred for several minutes and the organic layer was separated. The aqueous layer was re-extracted with CH2Cl2 (100 mL x 2). The combined extracts were dried with MgSO4 and concentrated to leave a dark brown solid, which was passed through a short silica column, eluting with CH2Cl2 (100percent). The resulting fraction was dried under vacuum, triturated with CH2Cl2 /hexanes (1:4; 50 mL) and solid formed was filtered and dried under vacuum to afford 5.36 g (82percent) of 12 as a light yellow solid. IR (KBr) max. cm-1: 3436, 3310 (NH2), 3032 (Ar-H), 2920 (Alph-H), 2246 (CN), 1610, 1512, 1418 (C=C). 1HNMR (500 MHz, CDCl3) = 4.47 (br. s, 2H, NH2); 6.88 (dd, 1H, J = 2.8, 8.2 Hz, H-5); 6.94 (br. s, 1H, H-3); 7.24 (d, 1H, J = 8.2 Hz, H-6); 13C NMR (125.7 MHz, CDCl3) = 95.17(C-1), 117.16 (CN), 118.15 (C-3), 121.60 (C-5), 129.03 (C-4), 133.60 (C-6), 150.47 (C-2). Calculated (percent) for C7H5BrN2(195.96); C: 42.67, H: 2.56, N: 14.22, found (percent); C: 42.60, H: 2.61, N: 14.17.To a solution of 2-amino-4-bromo-benzonitrile (1) (5.0 g, 0.0253 mol, 1.0 eqiv) in anhydrous toluene was added BF3.Et20 (3.76 mL, 0.0304 mol, 1.2 eqiv) slowly at room temperature. The reaction mixture was cooled to 0C followed by the addition of cyclohexanone (2) (3.9 mL, 0.0379, 1.5 eqiv) and the reaction mixture was heated to l00C for 4 h. After completion of reaction monitored by TLC, the reaction mixture was quenched with aq. NaOH solution upto pH= 10 and the reaction mixture was diluted with ethyl acetate. The organic layers were separated, dried over sodium sulphate and concentrated. The crude product was recrystallized from dichloromethane to obtained 6-bromo-l, 2, 3, 4- tetrahydroacridin-9-amine (118) (5.8 g, 82%) as pale yellow solid. (0078) *H NMR: DMSC 6 (400 MHz): d 8.13 (d, 1H, J= 8.8 Hz), 7.81 (s, 1H), 7.40-7.37 (m, 1H), 6.50 (bs, 2H), 2.82-2.79 (m, 2H), 2.55-2.52 (m, 2H), 1.82- (0079) 1.80 (m, 4H).LCMS: m/z 279.0 (M+2), Analysis calculated for Ci3Hi3BrN2

Molecular Weight:197.03
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:195.96361
Monoisotopic Mass:195.96361
Topological Polar Surface Area:49.8
Heavy Atom Count:10
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes