Sodium Hydroxide → HCID 59371249, compound

HRID 1479714Notes

Reaction equation

HRID 1479714 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]3=2)[CH:4]=[CH:3][C:2]=1[C:15](=O)[CH3:16].C([O-])(=O)C.[NH4+:22].N.O.[OH-].[Na+]>[Zn]>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]3=2)[CH:4]=[CH:3][C:2]=1[CH:15]([NH2:22])[CH3:16]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 12896473Azane;hydrateHCID 59371248HCID 59371248, compound

Product 1

HCID 59371249HCID 59371249, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

A solution of the oxime of 1-(benzo[h]quinolin-2yl)ethanone (2.60 g, 11.0 mmol) and ammonium acetate (1.05 g, 13.6 mmol) in a mixture consisting of 30% NH3/H2O/96% EtOH (39.5/26.3/26.3 ml) was stirred at ambient temperature for 30 minutes. Zinc in powder form (3.95 g, 60.4 mmol) was then added in small portions (at ambient temperature) over a period of 2 hours, and the resulting mixture was heated under reflux for 3 hours. The grey precipitate formed was filtered off under reduced pressure and the solvent was evaporated to give a residue that was alkalized with 10% NaOH, and extracted with Et2O (3×30 ml). The organic phases were combined, dried over anhydrous Na2SO4 and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography using MeOH as eluent to give 1.88 g (77% yield) of 1-(benzo[h]quinolin-2-yl)ethanamine in the form of an orange coloured oil.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customThe grey precipitate formed
  4. filtrationwas filtered off under reduced pressure
  5. customthe solvent was evaporated
  6. customto give a residue that
  7. extractionextracted with Et2O (3×30 ml)
  8. dry with materialdried over anhydrous Na2SO4
  9. customthe solvent evaporated under reduced pressure
  10. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-fe888041394f413cb374abe7ba093be4
Source dataset
uspto-grants-2016_08
Patent number
US09409867B2

Reaction notes

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