2-(4-cyanophenyl)acetamide synthesis

5synthesis methods

Product Name:2-(4-cyanophenyl)acetamide
CAS Number:117753-06-7
Molecular formula:C9H8N2O
Molecular Weight:160.17

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Yield:117753-06-7 350 mg

Reaction Conditions:

Stage #1: 4-cyanophenylacetic acidwith oxalyl dichloride;N,N-dimethyl-formamide in chloroform at 20; for 1 h;Inert atmosphere;Cooling with ice;
Stage #2: with ammonium hydroxide in tetrahydrofuran at 20; for 1 h;Inert atmosphere;Cooling with ice;

Steps:

2.1 2-(4-cyanophenyl)acetamide

Under a nitrogen atmosphere,(4-cyanophenyl) acetic acid (500 mg)In chloroform (6.0 mL) solution,Ice bath under cooling,Oxalyl chloride (620 mg) and N,After the addition of N- dimethylformamide (1 drop),And the mixture was stirred at room temperature for 1 hour.The reaction mixture was concentrated under reduced pressure.Residue of tetrahydrofuran (7.0 mL) ice bath under cooling to a suspension,28%After adding aqueous ammonia (3.00 mL),And the mixture was stirred at room temperature for 1 hour.Reaction solution of saturated sodium hydrogen carbonate aqueous solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting solid was washed with diisopropyl ether to give the title compound (350 mg) as a pale yellow solid.

References:

JP2015/78127,2015,A Location in patent:Paragraph 0089