Hydrochloric Acid → HCID 18327558, compound

HRID 1250408Notes

Reaction equation

HRID 1250408 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])C.[H-].[Na+].[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27]Br)=[CH:22][CH:21]=1)([O-:19])=[O:18].Cl.[OH-].[K+]>CN(C)C=O.CO.O.C(OCC)(=O)C>[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:14]=[C:6]2[C:4]([OH:3])=[O:5])=[CH:22][CH:21]=1)([O-:19])=[O:18]

Participants

9

Reactant 5

HCID 313Hydrochloric Acid2×HCID 14797Potassium HydroxideHCID 24758Sodium hydrideHCID 73125Ethyl indole-2-carboxylateHCID 792664-Nitrophenethyl bromide

Product 1

HCID 18327558HCID 18327558, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

1H-Indole-2-carboxylic acid ethyl ester(1.027 g, 5.4 mmol) was dissoved in 15 ml of dry dimethylformamide and stirred under nitrogen in an ice-bath. Sodium hydride (60% in paraffin oil; 274 mg, 6.85 mmol) was added and the solution stirred at room temperature for 1.5 hours. To the reaction mixture 2-(4-nitrophenyl)ethyl bromide (1.29 g, 5.6 mmol) was added and the solution was stirred overnight. The reaction mixture was heated for 4 hours at 60° C. After completion of the reaction (thin layer chromatography, chloroform/methanol/acetic acid 90:9:1) 20 ml of 2 N hydrochloric acid was added and the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried with magnesium sulfate, and evaporated to give an orange-red oil. The oily product was taken up in methanol/water (15 ml), and 1.2 g of potassium hydroxide were added. The reaction mixture was stirred overnight to complete the hydrolysis. Workup was achieved by addition of 2 N hydrochloric acid and extraction with ethyl acetate. Washing of the ethyl acetate layer with water, drying with magnesium sulfate, and evaporation in vacuo gave 1(2-(4-nitrophenyl)-ethyl)-1H-indole-2-carboxylic acid. MS: 310.2.

Workup

  1. stirringthe solution stirred at room temperature for 1.5 hours
  2. stirringthe solution was stirred overnight
  3. additionwas added
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried with magnesium sulfate
  7. customevaporated
  8. customto give an orange-red oil
  9. stirringThe reaction mixture was stirred overnight
  10. customthe hydrolysis
  11. washWashing of the ethyl acetate layer with water
  12. dry with materialdrying with magnesium sulfate, and evaporation in vacuo

Sources & evidence

ORD record
ord-1dbc1fd73baa4d66abf9579daaf1ee62
Source dataset
uspto-grants-2002_01
Patent number
US06337344B1

Reaction notes

Loading…