Ethyl Acetate → 7-Acetyl-5-nitroindole

HRID 1275087Notes

Reaction equation

HRID 1275087 reaction equation
C(C1[CH:4]=[C:5]([N+:12]([O-:14])=[O:13])[CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2)#N.[CH3:15][Mg+].[Br-].[OH-].[Na+].CCO[C:23]([CH3:25])=[O:24]>C1COCC1.CCCCCC>[C:23]([C:25]1[CH:4]=[C:5]([N+:12]([O-:14])=[O:13])[CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2)(=[O:24])[CH3:15]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 154534677-Cyano-5-nitroindoleHCID 178418689HCID 178418689, compound

Product 1

HCID 155414347-Acetyl-5-nitroindoleYield 26%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 7-cyano-5-nitroindole (0.7 g, 4.4 mmol) in 20 mL of THF was added 5. 0 mL of MeMgBr (3.0 M) and the resulting reaction mixture was stirred for 12 h at 25° C. Reaction was quenched by adding 10 mL of 1.0 N aqueous HCl. Reaction mixture was basified with 3 N aqueous NaOH and aqueous solution was extracted with EtOAc several times. Organic extracts were dried over MgSO4 and concentrated in vacuo to provide oily residue which was subjected to column chromatography (50% EtOAc/Cy.hexane) to yield 0.20 g (1.2 mmol, 26%) of the desired product.

Workup

  1. customReaction
  2. customwas quenched
  3. additionby adding 10 mL of 1.0 N aqueous HCl
  4. customReaction mixture
  5. extractionwas extracted with EtOAc several times
  6. dry with materialOrganic extracts were dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto provide oily residue which

Sources & evidence

ORD record
ord-f623e59e15214d28a6fefb0c14f15b1e
Source dataset
uspto-grants-2000_12
Patent number
US06159998

Reaction notes

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