Sodium Hydroxide → HCID 21914147, compound

HRID 887934Notes

Reaction equation

HRID 887934 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

Conditions

Temperature
57.5 °C

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-3-yl)-1H-indole.

Workup

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

Sources & evidence

ORD record
ord-1cfe4b0788f641c9b78a406760930c4e
Source dataset
uspto-grants-2012_08
Patent number
US08247432B2

Reaction notes

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