Hydrochloric Acid → HCID 54047355, compound

HRID 2293777Notes

Reaction equation

HRID 2293777 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[C:16]([C:20]([O:22]C)=[O:21])[NH:17]2)=[CH:13][CH:12]=1.[OH-].[K+].Cl>O1CCOCC1.O>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[C:16]([C:20]([OH:22])=[O:21])[NH:17]2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 54363952HCID 54363952, compound

Product 1

HCID 54047355HCID 54047355, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 6-[(2-(2-hydroxyethoxy)ethoxy)ethoxy]indole-2-carboxylate (V, EXAMPLE 3, 2.9 g) and potassium hydroxide (1.0 g) are dissolved in dioxane (25 ml) and water (5 ml). The reaction is warmed to 50° for 3 hours. The reaction is neutralized by the addition of hydrochloric acid (1N, 17 ml), extracted with THF/chloroform (50/50, 3×), washed with saline and concentrated under reduced pressure with heat. The material is purified by flash column chromatography eluting with methanol/chloroform/acetic acid (5/94/1). The appropriate fractions are pooled and concentrated to give the title compound, MS theory=309.1212, found=309.1208.

Workup

  1. temperatureThe reaction is warmed to 50° for 3 hours
  2. extractionextracted with THF/chloroform (50/50, 3×)
  3. washwashed with saline
  4. concentrationconcentrated under reduced pressure
  5. temperaturewith heat
  6. customThe material is purified by flash column chromatography
  7. washeluting with methanol/chloroform/acetic acid (5/94/1)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b6f1b4bb7dc74f5993f1a3bb23fa36d5
Source dataset
uspto-grants-1997_11
Patent number
US05686610

Reaction notes

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