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

HRID 21590

Reaction equation

HRID 21590 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0e93488b29b740aba879b81f4633c0a3
Source dataset
uspto-grants-1995_06
Patent number
US05424329

Linked notes

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