Methanol → 2-Chloro-5-(cyclopropanecarboxamidomethyl)benzoic acid

反応式

[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14]([CH:16]2[CH2:18][CH2:17]2)=[O:15])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].CO.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14]([CH:16]2[CH2:18][CH2:17]2)=[O:15])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

参加物

実験手順

To a solution of methyl 2-chloro-5-(cyclopropanecarboxamidomethyl)benzoate (10.0 g, 30 mmol) in THF: methanol (10:20 mL) was added aqueous solution of NaOH (6.0 g, 140 mmol). The reaction mixture was refluxed for 3-5 h. The reaction mixture was concentrated, diluted with water and acidified with dilute HCl. The reaction mixture was extracted with 10% MeOH:DCM and concentrated to afford 4.0 g of desired product. 1H NMR (300 MHz, DMSO de): δ 0.67 (m, 4H), 1.59 (m, 1H), 4.28 (d, J=6.0 Hz, 2H), 7.37-7.50 (m, 2H), 7.65 (s, 1H), 8.64 (m, 1H), 13.40 (br s, 1H).