Sodium Hydroxide → HCID 21914147, compound

HRID 1246213Notes

Reaction equation

HRID 1246213 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])[O:15][N:14]=1)(=O)C.[OH-].[Na+]>C(O)C.C(Cl)Cl>[CH2:18]([C:16]1[O: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 21914106HCID 21914106, compound

Product 1

HCID 21914147HCID 21914147, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of compound 89 (0.0035 mole) in ethanol (60 ml) was treated with 3M NaOH (60 ml), and the reaction mix was heated to 55–60° C. for 5.5 hours. The reaction was rapidly cooled in an ice bath, diluted with DCM, and treated with cold distilled water. The layers were separated and the aqueous fraction was extracted three times with DCM. The organic fractions were combined, washed once with 1M NaOH, and dried over Na2SO4 and concentrated in vacuo. The residue was purified by prep column chromatography, yielding 0.45 g of 2,3-dihydro-2-(5-propyl-1,2,4-oxadiazol-3yl)-1H-indole.

Workup

  1. additionthe reaction mix
  2. temperaturewas heated to 55–60° C. for 5.5 hours
  3. temperatureThe reaction was rapidly cooled in an ice bath
  4. additiontreated
  5. distillationwith cold distilled water
  6. customThe layers were separated
  7. extractionthe aqueous fraction was extracted three times with DCM
  8. washwashed once with 1M NaOH
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by prep column chromatography

Sources & evidence

ORD record
ord-404577d285bd4c88a72472ae9f2eb421
Source dataset
uspto-grants-2006_10
Patent number
US07125891B2

Reaction notes

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