ChemicalBook CAS DataBase List 4-Amino-β-oxobenzenepropanenitrile

4-Amino-β-oxobenzenepropanenitrile synthesis

5synthesis methods

Product Name:4-Amino-β-oxobenzenepropanenitrile
CAS Number:59443-94-6
Molecular formula:C9H8N2O
Molecular Weight:160.17

3383-43-5
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59443-94-6
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Yield:59443-94-6 48%

Reaction Conditions:

with iron;acetic acid in ethanol;water at 20; for 3 h;

Steps:

71.1 Step-1:
Synthesis of 3-(4-aminophenyl)-3-oxopropanenitrile (Intermediate 1)

To a solution of SM (1 g, 5.2 mmol) in acetic acid:EtOH:water (1:1:0.5, 35 mL) was added iron powder (3.89 g, 12.6 mmol) in portions, and the mixture was stirred at room temperature for 3 hours.
After the reaction completed, the reaction mixture was filtered through a celite pad and washed with ethyl acetate, and the filtrate was distilled off under reduced pressure to obtain a residue.
The residue was diluted with ethyl acetate, and washed with a saturated sodium bicarbonate solution, water and brine.
The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was distilled off under reduced pressure to obtain Intermediate 1 (400 mg).
Yield: 48%, ¹H NMR (400 MHz, DMSO-d₆) δ 4.47 (s, 2H), 6.29 (s, 2H), 6.57 (d, J=8.80 Hz, 2H), 7.64 (d, J=8.31 Hz, 2H) and LC-MS (M+1): 161.05.

References:

EP3640253,2020,A1 Location in patent:Paragraph 0363-0365