Hydrochloric Acid → 2-(5-Ethyl-1H-indol-3-ylmethyl)-malonic acid diethyl ester

HRID 1726412Notes

Reaction equation

HRID 1726412 reaction equation
[CH3:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]2[NH:9][CH:10]=[C:11]([CH2:12]N(C)C)[C:5]=2[CH:4]=1.[C:16]([O:24][CH2:25][CH3:26])(=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].[Na].Cl>>[CH2:21]([O:20][C:18](=[O:19])[CH:17]([CH2:12][C:11]1[C:5]2[C:6](=[CH:7][CH:8]=[C:3]([CH2:2][CH3:1])[CH:4]=2)[NH:9][CH:10]=1)[C:16]([O:24][CH2:25][CH3:26])=[O:23])[CH3:22]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 2696955-EthylgramineHCID 5360545Sodium

Product 1

HCID 588430642-(5-Ethyl-1H-indol-3-ylmethyl)-malonic acid diethyl esterYield 85.1%

Conditions

Temperature
120 °C

Procedure

5-Ethylgramine (1.25 g, 6.18 mmol) was combined with diethyl malonate (2.85 mL, 18.54 mmol) and heated to 120° C. until a homogeneous solution was formed. To this mixture was added sodium metal (100 mg, 4.36 mmol) and the mixture was stirred at 120° C. for 24 hours. TLC indicated the completion of the reaction. The reaction was allowed to cool to room temperature and a solution of 5% HCl (aqueous) was slowly added to the mixture and the resulting product was extracted with EtOAc. The organic layer was washed with saturated sodium bicarbonate, dried over anhydrous magnesium sulafate, filtered and evaporated to give compound 12 as a white solid (1.67 g; 85% yield; M+1=318.4). The product was taken into the next step without purification.

Workup

  1. customwas formed
  2. customthe completion of the reaction
  3. temperatureto cool to room temperature
  4. extractionthe resulting product was extracted with EtOAc
  5. washThe organic layer was washed with saturated sodium bicarbonate
  6. dry with materialdried over anhydrous magnesium sulafate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-3e6f8a5d28f749c49679a31f9a749897
Source dataset
uspto-grants-2009_02
Patent number
US07491831B2

Reaction notes

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