반응 #67796

반응 방정식

lithium bis(trimethylsilyl)amide

3-fluoroisonicotinic acid

2-chloro-4-iodoaniline

lithium bis(trimethylsilyl)amide

→

3-[(2-chloro-4-iodophenyl)amino]isonicotinic acid

용매

tetrahydrofuran

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe resulting green colored solution was stirred for 15 min
2. 2
   workup.ADDITIONTo this green colored solution the lithiated acid solution was added
3. 3
   기타The cold bath was removed
4. 4
   workup.STIRRINGstirred overnight
5. 5
   여과The mixture was filtered
6. 6
   workup.ADDITIONthe crude was diluted with EtOAc (400 ml)
7. 7
   세척It was then washed with dilute HCl (25 ml), H2O (25 ml)
8. 8
   기타dried
9. 9
   기타During concentration of the solvent, 3-[(2-chloro-4-iodophenyl)amino]isonicotinic acid was separated out as an yellow solid

실험 절차

To suspension of 3-fluoroisonicotinic acid (2.00 g, 14.17 mmol, in tetrahydrofuran (50 ml) at −78° C. was added lithium bis(trimethylsilyl)amide (14.3 ml, 17.01 mmol). The dark colored suspension was stirred for 15 min. In another flask, to a solution of 2-chloro-4-iodoaniline (4.7 g, 18.43 mmol) in THF (50 ml) was added lithium bis(trimethylsilyl)amide (24.9 ml, 29.77 mmol) at −78° C. under N2. The resulting green colored solution was stirred for 15 min. To this green colored solution the lithiated acid solution was added. The cold bath was removed, allowed to warm to room temperature, and stirred overnight. The mixture was filtered, and the crude was diluted with EtOAc (400 ml). It was then washed with dilute HCl (25 ml), H2O (25 ml), and dried. During concentration of the solvent, 3-[(2-chloro-4-iodophenyl)amino]isonicotinic acid was separated out as an yellow solid. (1.3 g, 24%)

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