Ammonia → 5-Methoxy-3-(1-methylethoxy)-1H-indole-2-carboxamide

HRID 21590

반응식

HRID 21590 반응식
[NH2-:1].[Li+].N.[Li].[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:16](OC)=[O:17])=[C:10]2[O:20][CH:21]([CH3:23])[CH3:22]>O1CCCC1>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:16]([NH2:1])=[O:17])=[C:10]2[O:20][CH:21]([CH3:23])[CH3:22]

참가 물질

6

반응물 4

HCID 222Ammonia2회HCID 24532Lithium amideHCID 3028194LithiumHCID 13840803methyl 5-methoxy-3-(1-methylethoxy)-1H-indole-2-carboxylate

생성물 1

HCID 107530635-Methoxy-3-(1-methylethoxy)-1H-indole-2-carboxamide수율 76%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Lithium amide in liquid ammonia is prepared as described by Unangst PC and Carethers ME, J. Heterocyclic Chem. 1984;21:709, from lithium metal ribbon (0.059 g, 8.5 mmol). A solution of methyl 5-methoxy-3-(1-methylethoxy)-1H-indole-2-carboxylate (0.15 g, 0.57 mmol; Unangst PC, et al., J, Heterocyclic Chem. 1987;24:811) in 4.0 mL of tetrahydrofuran is added dropwise. The mixture is stirred for 1 hour and the excess ammonia is allowed to evaporate. The residue is diluted with ethyl acetate, and the organic layer is washed with 1.0N HCl brine, saturated sodium bicarbonate solution, and brine again. The solution is dried (anhydrous magnesium sulfate) and evaporated. Recrystallization of the residue from ethyl acetatehexane gives 0.11 g (76%) of product; mp 138.5°-140° C.

후처리

  1. customto evaporate
  2. additionThe residue is diluted with ethyl acetate
  3. washthe organic layer is washed with 1.0N HCl brine, saturated sodium bicarbonate solution, and brine again
  4. dry with materialThe solution is dried (anhydrous magnesium sulfate)
  5. customevaporated
  6. customRecrystallization of the residue from ethyl acetatehexane

출처 및 근거

ORD 기록
ord-0e93488b29b740aba879b81f4633c0a3
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424329

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