N-(2-(1H-Indene-1-yl)ethyl)hydroxylamine → 1H-Indene-3-ethanamine

HRID 1534797Notes

Reaction equation

HRID 1534797 reaction equation
[CH:1]1([CH2:10][CH2:11][NH:12]O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1>C(O)(=O)C.[Zn]>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]([CH2:10][CH2:11][NH2:12])=[CH:2]1

Participants

4

Reactant 1

HCID 19908298N-(2-(1H-Indene-1-yl)ethyl)hydroxylamine

Product 1

HCID 5339401H-Indene-3-ethanamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

N-(2-(1H-Indene-1-yl)ethyl)hydroxylamine (85 mg, 0.486 mmol) was added to a slurry of zinc dust (104 mg, 1.59 mmol) in glacial acetic acid (3 ml), and the mixture was heated at 65° for 2 hours. The mixture was cooled and filtered, then made basic with conc. ammonium hydroxide and extracted with ether. The ether layer was washed with water, then with brine, dried ober sodium sulfate, filtered, and evaporated to dryness in vacuo. The residue was chromatographed on a silica gel column eluted with 90:10:1 of CH2Cl2 :MeOH:NH4OH. The product fractions were evaporated to dryness in vacuo to give (2-(1H-indene-3-yl)ethyl)amine.

Workup

  1. temperaturethe mixture was heated at 65° for 2 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. extractionextracted with ether
  5. washThe ether layer was washed with water
  6. dry with materialwith brine, dried ober sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness in vacuo
  9. customThe residue was chromatographed on a silica gel column
  10. washeluted with 90:10:1 of CH2Cl2
  11. customThe product fractions were evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-d4d669521c0642a4a1a8a890b93ac5cd
Source dataset
uspto-grants-1992_02
Patent number
US05091387

Reaction notes

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