반응 #545174

반응 방정식

4-fluorosalicylic acid chloride

N,N-diisopropylethyl amine

acetonitrile hydrochloride

→

N-cyanomethyl-4-fluoro-2-hydroxy-benzamide

수율 65.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   농축the solution was concentrated under reduced pressure
2. 2
   workup.ADDITIONdiluted with ethyl acetate
3. 3
   세척washed successively with 2 N HCl and saturated aq NaCl
4. 4
   건조The resulting solution was dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   여과filtered
8. 8
   세척rinsed with heptane

실험 절차

A solution of 4-fluorosalicylic acid chloride (Example 1, 10 g, 57.3 mmol) in dichloromethane (114 mL) was treated with N,N-diisopropylethyl amine (25 mL, 143 mmol) and acetonitrile hydrochloride (7.95 g, 85.9 mmol). After stirring at 35° C. for 24 h, the solution was concentrated under reduced pressure, diluted with ethyl acetate, and washed successively with 2 N HCl and saturated aq NaCl. The resulting solution was dried over MgSO4, filtered and concentrated. The resulting solid was suspended in dichloromethane, filtered and rinsed with heptane to give N-cyanomethyl-4-fluoro-2-hydroxy-benzamide (7.20 g, 65%): 1H NMR (DMSO-d6 300 MHz) δ 12.16 (br s, 1 H), 9.17 (t, J=5.3 Hz, 1 H), 7.88 (dd, J, =8.7 Hz, J2=6.3 Hz, 1 H), 6.81–6.73 (m, 2 H), 4.32 (d, J=5.7 Hz, 2 H).

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