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

HRID 1351843Notes

Reaction equation

HRID 1351843 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 by column chromatography on silica gel (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-bdcd8bdcc3c54074a3ca882f012aa7a9
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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