1,5,6,7-Tetrahydro-4H-indol-4-one → 1,5,6,7-Tetrahydro-indol-4-one oxime

HRID 481765Notes

Reaction equation

HRID 481765 reaction equation
C([O-])(=O)C.[Na+].Cl.[NH2:7][OH:8].O=[C:10]1[CH2:18][CH2:17][CH2:16][C:15]2[NH:14][CH:13]=[CH:12][C:11]1=2>O.C(O)C>[N:7](=[C:10]1[CH2:18][CH2:17][CH2:16][C:15]2[NH:14][CH:13]=[CH:12][C:11]1=2)[OH:8]

Participants

6

Reactant 3

HCID 2802291,5,6,7-Tetrahydro-4H-indol-4-oneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 9156771,5,6,7-Tetrahydro-indol-4-one oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 6.08 g of sodium acetate, 5.15 g of hydroxylamine hydrochloride, and 5.25 g of 4-keto-4,5,6,7-tetrahydro indole in 12 mL of water and 36 mL of ethanol was heated at 50° C. for 3 hr, quenched in water, extracted with ethyl acetate and dried over magnesium sulfate. The solvents were removed in vacuo to give a mixture of oxime isomers which was characterized by NMR and Mass spectroscopy.

Workup

  1. customquenched in water
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customThe solvents were removed in vacuo
  5. customto give

Sources & evidence

ORD record
ord-af4ae2cf1e3246a0ae83c89085e61ea9
Source dataset
uspto-grants-1998_08
Patent number
US05789587

Reaction notes

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