Sodium Hydroxide → HCID 21914127, compound

HRID 887932Notes

Reaction equation

HRID 887932 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:13]1[N:17]=[C:16]([CH2:18][CH2:19][CH3:20])[NH:15][N:14]=1)(=O)C.[OH-].[Na+]>C(O)C.C(OCC)(=O)C>[CH2:18]([C:16]1[NH:15][N:14]=[C:13]([CH:5]2[CH2:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[NH:4]2)[N:17]=1)[CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21914092HCID 21914092, compound

Product 1

HCID 21914127HCID 21914127, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the compound 91 (0.42 g) in ethanol (25 ml) was treated with an aqueous NaOH solution (3 M, 25 mL) and the reaction mix was refluxed for 24 hours. The reaction was cooled, diluted with ethyl acetate, and treated with cold distilled water. The layers were separated and the aqueous fraction was extracted 5 times with ethyl acetate and the combined organic fractions were dried, concentrated and purified by preparatory column chromatography yielding 2,3-dihydro-2-(5-propyl-1H-1,2,4-triazol-3-yl)-1H-indole.

Workup

  1. additionthe reaction mix
  2. temperaturewas refluxed for 24 hours
  3. temperatureThe reaction was cooled
  4. additiontreated
  5. distillationwith cold distilled water
  6. customThe layers were separated
  7. extractionthe aqueous fraction was extracted 5 times with ethyl acetate
  8. customthe combined organic fractions were dried
  9. concentrationconcentrated
  10. custompurified by preparatory column chromatography

Sources & evidence

ORD record
ord-8f289a655286477cba3d088e1160d624
Source dataset
uspto-grants-2012_08
Patent number
US08247432B2

Reaction notes

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