Cyclopropanecarbonyl chloride → Methyl 2-chloro-5-(cyclopropanecarboxamidomethyl)benzoate

反応式

[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9].CCN(C(C)C)C(C)C.[CH:23]1([C:26](Cl)=[O:27])[CH2:25][CH2:24]1>C1COCC1>[Cl:13][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH:1][C:26]([CH:23]2[CH2:25][CH2:24]2)=[O:27])=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

参加物

実験手順

To a solution of methyl 5-(aminomethyl)-2-chlorobenzoate (15.0 g, 75 mmol) in dry THF (150 mL) was added DIPEA (15 mL) under nitrogen atmosphere. Cyclopropanecarbonyl chloride was added to the reaction mixture at 10° C. and (11.81 g, 113 mmol). The reaction mixture was stirred at RT for 5-6 h. The reaction mixture was quenched with ice water and extracted with ethyl acetate. The organic layer was washed with dilute HCl, followed with sodium bicarbonate solution and concentrated to afford 10.0 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 0.69 (m, 4H), 1.59 (m, 1H), 3.86 (s, 3H), 4.29 (d, J=6.0 Hz, 2H), 7.43 (d, J=6.6 Hz, 1H), 7.53 (d, J=8.4 Hz, 1H), 7.67 (s, 1H), 8.64 (br s, 1H); MS (m/z): 268.16 (M+H)+.