1-(Aminomethyl)-1,2,3,4-tetrahydronaphthalen-1-ol → 6,7,8,9-tetrahydro-5H-benzo(7)annulen-6-one

HRID 2299629Notes

Reaction equation

HRID 2299629 reaction equation
N[CH2:2][C:3]1([OH:13])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1.N([O-])=O.[Na+]>C(O)(=O)C.O.C(OCC)(=O)C>[CH:8]1[C:7]2[CH2:6][CH2:5][CH2:4][C:3](=[O:13])[CH2:2][C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 2

HCID 129148591-(Aminomethyl)-1,2,3,4-tetrahydronaphthalen-1-olHCID 23668193Sodium Nitrite

Product 1

HCID 124880816,7,8,9-tetrahydro-5H-benzo(7)annulen-6-oneYield 54.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-aminomethyl-1-hydroxy-1,2,3,4-tetrahydronaphthalene (19 g) in 10% acetic acid in water (380 ml) was dropwise added sodium nitrite (11 g) in water (56 ml) at 5° C., and the mixture was stirred at the same temperature for 2 hours. The resulting mixture was diluted with ethyl acetate and separated. The organic layer was successively washed with water, saturated aqueous sodium hydrogencarbonate and brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified. by column chromatography on silica gel (hexane-ethyl acetate) to give 5,7,8,9-tetrahydrobenzocyclohepten-6-one (9.3 g).

Workup

  1. customat 5° C.
  2. customseparated
  3. washThe organic layer was successively washed with water, saturated aqueous sodium hydrogencarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-bb683c0df7a54076945604687f814d4d
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

Loading…