تفاعل #87605

معادلة التفاعل

methyl 2-chloro-5-(cyclopropanecarboxamidomethyl)benzoate

methanol

NaOH

→

desired product

المردود 52.6%

2-chloro-5-(cyclopropanecarboxamidomethyl)benzoic acid

المردود 52.6%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was refluxed for 3-5 h
2. 2
   تركيزThe reaction mixture was concentrated
3. 3
   workup.ADDITIONdiluted with water
4. 4
   استخلاصThe reaction mixture was extracted with 10% MeOH
5. 5
   تركيزDCM and concentrated

الإجراء التجريبي

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).

المصدر