Hydrochloric Acid → 3-(Aminomethyl)-5-bromobenzonitrile

반응식

O.NN.[Br:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([CH2:13][N:14]2C(=O)C3C(=CC=CC=3)C2=O)[CH:12]=1)[C:8]#[N:9].Cl>CCO>[NH2:14][CH2:13][C:11]1[CH:10]=[C:7]([CH:6]=[C:5]([Br:4])[CH:12]=1)[C:8]#[N:9]

참가 물질

실험 절차

Hydrazine hydrate (85%, 1.31 g) was added to a suspension of 3-bromo-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzonitrile (3.50 g, 10.3 mmol) in EtOH (60 mL). The mixture was refluxed for 3 h. Then, at room temperature, 2 N HCl (20 mL) was added (pH=3), and the mixture was filtered and the solid was rinsed with water (20 mL×2). The filtrate was evaporated to about 50 mL and filtered again. After addition of NaHCO3 (pH=9), the filtrate was extracted with CH2Cl2 (50 mL×3). The combined extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product. It was recrystallized from MeOH-Et2O yielding the product (1.40 g, 55%) as colorless fine needles. 1H NMR (400 MHz, D2O): δ 7.92 (m, 1H), 7.84 (m, 1H), 7.69 (m, 1H), 4.11 (s, 2H); 13C NMR (400 MHz, D2O): δ 137.1, 135.9, 135.8, 131.7, 123.0, 117.7, 113.8, 42.0; MS: m/z 209.0 (M+-HCl); HPLC: retention time: 9.313 min; purity: 98.4%.