ChemicalBook CAS DataBase List N-(3-Formylphenyl)acetamide

N-(3-Formylphenyl)acetamide synthesis

11synthesis methods

Product Name:N-(3-Formylphenyl)acetamide
CAS Number:59755-25-8
Molecular formula:C9H9NO2
Molecular Weight:163.17

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Yield: 95%

Reaction Conditions:

with pyridinium chlorochromate in dichloromethane;N,N-dimethyl-formamide at 25; for 2 h;Inert atmosphere;

Steps:

5
/V-(3-(hydroxymethyl)phenyl)acetamide (100 mg, 0.6 mmol), PCC (390 mg, 1.8 mmol), and Celite (100 mg) were suspended in a mixture of CH2CI2 (6 mF) and DMF (0.5 mF). The mixture was stirred at 25 °C for 2 h. The solvent was evaporated in vacuo and the residue was purified by column chromatography (hexane: EtOAc; 1:2). The product was obtained as a white solid (95 mg, 95 %). (0126) NMR (500 MHz, CDCl₃) d (ppm) 9.99 (s, 1H), 8.02 - 7.98 (m, 1H), 7.92 - 7.86 (m, 1H), 7.70 (s, (0127) 1H), 7.63 (d, J= 7.6 Hz, 1H), 7.54 - 7.45 (m, 1H), 2.23 (s, 3H); (0128) ¹³C NMR (126 MHz, CDCl₃) d (ppm) 192.2, 168.9, 139.1, 137.3, 130.0, 125.9, 125.8, 120.5, 24.8; (0129) HRMS calcd for C₉H₈N0₂ [M-Hf 162.0561, found 162.0560

References:

MASARYKOVA UNIVERZITA;PARUCH, Kamil;CARBAIN, Benoit;HAVEL, Stepan;DAMBORSKY, Jiri;BREZOVSKY, Jan;DANIEL, Lukas;SISAKOVA, Alexandra;NIKULENKOV, Fedor;KREJCI, Lumir WO2019/201865, 2019, A1 Location in patent:Page/Page column 14; 20