ChemicalBook CAS DataBase List 3-(aminomethyl)-5-bromobenzonitrile

3-(aminomethyl)-5-bromobenzonitrile synthesis

8synthesis methods

Product Name:3-(aminomethyl)-5-bromobenzonitrile
CAS Number:1177558-50-7
Molecular formula:C8H7BrN2
Molecular Weight:211.06

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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1177558-50-7
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Yield: 55%

Reaction Conditions:

with hydrazine hydrate in ethanol;water for 3 h;Reflux;

Steps:

48 3-(Aminomethyl)-5-bromobenzonitrile
Example 48 3-(Aminomethyl)-5-bromobenzonitrile 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%.

References:

Glaxo Group Limited US2009/203657, 2009, A1 Location in patent:Page/Page column 54