반응 #89789

반응 방정식

4-hydrazinobenzoic acid

isopropylmethylketone

→

desired product

수율 80.1%

2,3,3-Trimethyl-5-carboxy-3H-indole

수율 80.1%

용매

acetic acid

반응 조건

후처리

1. 1
   온도under reflux in an oil bath for 20 h
2. 2
   기타was evaporated off under reduced pressure and to it
3. 3
   workup.ADDITIONwas added a saturated aqueous solution of NaHCO3 (50 mL)
4. 4
   세척washed with CH2Cl2 (3×40 mL)
5. 5
   추출extracted with CH2Cl2 (3×50 mL)
6. 6
   건조The combined organic solution was then dried with Na2SO4
7. 7
   여과filtered
8. 8
   농축concentrated to dryness under reduced pressure

실험 절차

A solution of 4-hydrazinobenzoic acid (10.0 g, 65.7 mmol), isopropylmethylketone (21.1 mL, 197 mmol) in acetic acid (35 mL) was heated under reflux in an oil bath for 20 h. After cooling to ambient temperature the solvent was evaporated off under reduced pressure and to it was added a saturated aqueous solution of NaHCO3 (50 mL) and washed with CH2Cl2 (3×40 mL). The pH of the aqueous solution was adjusted with 1 M aqueous HCl to ca. 2, and then extracted with CH2Cl2 (3×50 mL). The combined organic solution was then dried with Na2SO4, filtered and concentrated to dryness under reduced pressure to yield the desired product (10.7 g, 80%) as a brownish solid.

출처