Water → Diethyl 1H-indole-2,6-dicarboxylate

HRID 1748242노트

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HRID 1748242 반응식
[CH2:1]([O:3][C:4](=[O:22])[C:5](=O)[CH2:6][C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][C:8]=1[N+:18]([O-])=O)[CH3:2].O.CCOC(C)=O>C(O)(=O)C.[Zn]>[NH:18]1[C:8]2[C:7](=[CH:17][CH:16]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]=2)[CH:6]=[C:5]1[C:4]([O:3][CH2:1][CH3:2])=[O:22]

참가 물질

6

반응물 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 58767563Ethyl 4-(3-ethoxy-2,3-dioxopropyl)-3-nitrobenzoate

생성물 1

HCID 44754779Diethyl 1H-indole-2,6-dicarboxylate수율 58.9%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 176Acetic Acid용매

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온도
75 °C

실험 절차

Ethyl 4-(3-ethoxy-2,3-dioxopropyl)-3-nitrobenzoate (91 g, 0.29 mol) is suspended in 800 mL of acetic acid and it is heated with stirring to 75° C. Once the solid is dissolved, water (600 mL) is added. Zinc dust (189 g, 2.9 mol) is added carefully in small portions and the reaction temperature is kept below 85° C. The mixture is then stirred vigorously for 1 hour after the addition. EtOAc (1500 mL) is added and the mixture was filtered through Celite. The solid is washed with more EtOAc (1500 mL) and the filtrates are combined, washed twice with water (1500 mL), four times with saturated NaHCO3 (1000 mL), and once with brine (1000 mL). The filtrate is dried (Na2SO4), filtered, and concentrated to afford the crude compound which was recrystallized from toluene to afford the title compound (44.6 g, 58%) as a yellow powder.

후처리

  1. temperatureit is heated
  2. dissolutionOnce the solid is dissolved
  3. customis kept below 85° C
  4. stirringThe mixture is then stirred vigorously for 1 hour
  5. additionafter the addition
  6. filtrationthe mixture was filtered through Celite
  7. washThe solid is washed with more EtOAc (1500 mL)
  8. washwashed twice with water (1500 mL), four times with saturated NaHCO3 (1000 mL)
  9. dry with materialThe filtrate is dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto afford the crude compound which
  13. customwas recrystallized from toluene

출처 및 근거

ORD 기록
ord-dd2fd7a2a70443f6ba3298a9a22a5d97
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150577B2

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