Water → HCID 13274764, compound

HRID 1248108Notes

Reaction equation

HRID 1248108 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:6]2.[CH2:16]([CH:18]1[O:20][CH2:19]1)Cl.[OH-].[Na+].O>C(O)C.C(O)(=O)C>[O:20]1[CH2:19][CH:18]1[CH2:16][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:6]2

Participants

7

Reactant 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 13274763Ethyl 4-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 13274764HCID 13274764, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

4.2 g of 4-hydroxy 2-ethoxycarbonyl indole and 40 ml of epichlorohydrine are dissolved by heating in an inert atmosphere in 40 ml of absolute ethanol then 0.82 g of sodium hydroxide in pellet form is added and the mixture is taken to reflux for 5 hours. Water is added to the reaction mixture and it is neutralized by the addition of acetic acid. The solvents are evaporated in vacuo then extracted with methylene chloride. The organic solution is dried over sodium sulfate and the solvent is evaporated to dryness in vacuo. The residue is chromatographed over a column of silica gel. By elution with the ether-pentane (80-20 vol/vol) mixture, the expected compound is obtained (3.5 g), m.p.: 142°-144° C.

Workup

  1. temperatureto reflux for 5 hours
  2. customThe solvents are evaporated in vacuo
  3. extractionthen extracted with methylene chloride
  4. dry with materialThe organic solution is dried over sodium sulfate
  5. customthe solvent is evaporated to dryness in vacuo
  6. customThe residue is chromatographed over a column of silica gel
  7. washBy elution with the ether-pentane (80-20 vol/vol) mixture

Sources & evidence

ORD record
ord-861911ce23f241ab8de2e12152b80afc
Source dataset
uspto-grants-1985_06
Patent number
US04522824

Reaction notes

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