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

HRID 21590

反応式

HRID 21590 の反応式
[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]

参加物

6

反応物 4

HCID 222Ammonia2 回HCID 24532Lithium amideHCID 3028194LithiumHCID 13840803methyl 5-methoxy-3-(1-methylethoxy)-1H-indole-2-carboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0e93488b29b740aba879b81f4633c0a3
出典データセット
uspto-grants-1995_06
特許番号
US05424329

関連ノート

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