Hydroxylamine → HCID 87536207, compound

HRID 2070984Notes

Reaction equation

HRID 2070984 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH:10]=O)[CH:3]=[CH:2]1.[NH2:12][OH:13].[OH-].[Na+]>CCO.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2/[CH:10]=[N:12]\[OH:13])[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 2734629Indole-7-carboxaldehyde

Product 1

HCID 87536207HCID 87536207, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1H-indole-7-carbaldehyde (1 g, 6.9 mmol) in EtOH (30 mL), hydroxylamine (527 mg, 7.6 mmol) in water (10 mL) was added followed by 50% NaOH (1.38 g in 1.38 mL water) was added. After refluxing for 2 h, ethanol was removed under reduced pressure. Resultant slurry was extracted with ethylacetate. Organic layer was washed with water, brine and dried. Crude residue was column chromatographed on a silica gel eluting with (30% EtOAc/hexanes) to afford (Z)-1H-indole-7-carbaldehyde oxime in 80% yield.

Workup

  1. additionwas added
  2. temperatureAfter refluxing for 2 h
  3. customethanol was removed under reduced pressure
  4. extractionResultant slurry was extracted with ethylacetate
  5. washOrganic layer was washed with water, brine
  6. customdried
  7. customchromatographed on a silica gel eluting with (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b8a52e5249e14a1c8aa0062ad58950b8
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

Loading…