Hydrochloric Acid → HCID 13166911, compound

HRID 1421220Notes

Reaction equation

HRID 1421220 reaction equation
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[C:16]([O:21][CH2:22][CH3:23])(=[O:20])[C:17]([CH3:19])=O>C(O)C>[CH2:14]([O:13][C:11]([C:3]1[NH:2][C:10]2[C:5]([C:4]=1[C:17](=[CH2:19])[C:16]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:12])[CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12041Ethyl pyruvateHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 13166911HCID 13166911, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An ethanol solution saturated with gaseous hydrochloric acid containing 39.1 g (207 mmol) of ethyl 1H-indole-2-carboxylate and 45.3 ml (410 umol) of ethyl pyruvate is brought to approximately 60° C. for 3 h. The mixture is concentrated under reduced pressure and the residue is taken up in diethyl ether. The organic phase is washed with water and dried over sodium sulphate. The solvent is evaporated under reduced pressure and the residue is crystallized from cyclohexane. 45.4 g (158 mmol) of solid product are obtained, which product is used as is in the following stage.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulphate
  4. customThe solvent is evaporated under reduced pressure
  5. customthe residue is crystallized from cyclohexane

Sources & evidence

ORD record
ord-d234c0ac69c64765be038c555845ae86
Source dataset
uspto-grants-2000_06
Patent number
US06075021

Reaction notes

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