Pyridine → 2-chloro-N-(2-formylphenyl)acetamide

Temperature

20 °C

A solution of 2-aminobenzaldehyde (0.969 g, 8 mmol) and pyridine (1.618 mL, 20.00 mmol) in benzene (8 mL) was stirred at 5° C. under a dry nitrogen atmosphere. A solution of chloroacetyl chloride (0.765 mL, 9.60 mmol) in benzene (4 mL) was added dropwise to the reaction mixture. When the addition was complete, the reaction mixture was allowed to warm to 20° C., then was stirred at that temperature for 15 minutes. The reaction mixture was then washed with water (3×20 mL). The combined aqueous layers were extracted once with EtOAc (15 mL). The combined organic layers were dried (Na2SO4) and filtered. The filtrate was concentrated under reduced pressure to give a pale yellow solid. The solid was checked by TLC (9:1 hexane/EtOAc). A new spot with Rf lower than the starting material was evident. The crude solid was treated with THF/Et2O to provide the intermediate, 2-chloro-N-(2-formylphenyl)acetamide, as an off-white solid (892 mg, 56.4%) that was collected by filtration. 1H NMR (300 MHz, d6-DMSO) δ 11.43 (s, 1H), 10.01 (s, 1H), 8.32 (d, J=8.2 Hz, 1H), 7.94 (dd, J=7.7, 1.6 Hz, 1H), 7.76-7.69 (m, 1H), 7.39 (dt, J=7.5, 1.0 Hz, 1H), 4.47 (s, 2H). MS (DCI—NH3) m/z=198 (M+H)+, m/z=215 (M+NH4)+, m/z=232 (M+NH4+NH3)+.

1. additionWhen the addition
2. washThe reaction mixture was then washed with water (3×20 mL)
3. extractionThe combined aqueous layers were extracted once with EtOAc (15 mL)
4. dry with materialThe combined organic layers were dried (Na2SO4)
5. filtrationfiltered
6. concentrationThe filtrate was concentrated under reduced pressure
7. customto give a pale yellow solid

ORD record

ord-4ce32fe2de834c459228668974581a5a

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09138494B2