Ammonia → HCID 21714272, compound

HRID 650055Notes

Reaction equation

HRID 650055 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14]C2CCCCO2)=[C:7]2[C:3]=1[CH:4]=[C:5]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[NH:6]2.Cl.O.N>O1CCCC1>[OH:14][CH2:13][CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]2[C:7]=1[NH:6][C:5]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:4]2

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 962WaterHCID 21714286HCID 21714286, compound

Product 1

HCID 21714272HCID 21714272, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-methyl-7-[2-(2-tetrahydro-2H-pyranyl)oxyethoxy]-1H-indole-2-carboxylate (3.20 g, 9.21 mmol) was dissolved in tetrahydrofuran (70 ml), followed by adding thereto 2N hydrochloric acid (30 ml) at room temperature. The mixture was stirred at room temperature for 3 hours, after which water (200 ml) and then 28% aqueous ammonia were added thereto to neutralize (pH=7 to 8) the reaction mixture. Subsequently, the reaction mixture was extracted twice with ethyl acetate and the extract solution was washed with a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was crystallized from ethyl acetate to obtain ethyl 7-(2-hydroxyethoxy)-4-methyl-1H-indole-2-carboxylate (1.93 g).

Workup

  1. additionby adding
  2. customat room temperature
  3. extractionSubsequently, the reaction mixture was extracted twice with ethyl acetate
  4. washthe extract solution was washed with a 5% aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-e020b252a80d4c559a65f179fc0eb0e7
Source dataset
uspto-grants-2001_08
Patent number
US06271251B1

Reaction notes

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