Hydroxyamine hydrochloride → HCID 72295607, compound

HRID 1009535Notes

Reaction equation

HRID 1009535 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14](=O)[CH3:15])=[CH:4]1)[CH3:2].C(N1C2C(=CC=C(OC)C=2)C=C1)C.Cl.[OH:31][NH2:32].CC([O-])=O.[Na+]>CCO>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14](=[N:32][OH:31])[CH3:15])=[CH:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 59425473HCID 59425473, compoundHCID 59425954HCID 59425954, compound

Product 1

HCID 72295607HCID 72295607, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1-(1-ethyl-6-methoxy-1-H-indole-3-yl)ethanone (200 mg, 0.92 mmol), prepared from 1-ethyl-6-methoxy-1H-indole by the procedure described in example 1L, hydroxyamine hydrochloride (128 mg, 1.84 mmol), NaOAc (151 mg, 1.84 mmol) and EtOH (7 mL) is heated at 85° C. for 4 h. The reaction mixture is then partitioned between H2O and EtOAc. The organic phase is dried and concentrated in vacuo. Purification by column chromatography using EtOAc/CH2Cl2 (1/9) yields 1-(1-ethyl-6-methoxy-1-H-indole-3-yl)ethanone oxime as a white solid (189 mg, 92%).

Workup

  1. customThe reaction mixture is then partitioned between H2O and EtOAc
  2. customThe organic phase is dried
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-3b1e3aa0661e45209f2cd9a1c2f9614d
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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