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

HRID 1936966Notes

Reaction equation

HRID 1936966 reaction equation
N[CH2:2][C:3]1([OH:15])[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1.N([O-])=O.[Na+]>O1CCOCC1.C(O)(=O)C.O.C(OCC)(=O)C>[CH3:14][O:13][C:8]1[C:7]2[CH2:6][CH2:5][CH2:4][C:3](=[O:15])[CH2:2][C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 2

HCID 224629121-Aminomethyl-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-olHCID 23668193Sodium Nitrite

Product 1

HCID 127282361-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-oneYield 52%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-aminomethyl-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol (26.6 g) in 1,4-dioxane (60 ml), acetic acid (24 ml) and water (210 ml) was added sodium nitrite (9.7 g) in water (60 ml) dropwise at 5° C., and the mixture was stirred at the same temperature for 2.5 hours. The resulting mixture was diluted with ethyl acetate and separated. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed (hexane-ethyl acetate) over silica gel to afford 1-methoxy-5,7,8,9-tetrahydro-6H-benzocyclohepten-6-one (12.7 g).

Workup

  1. customseparated
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed (hexane-ethyl acetate) over silica gel

Sources & evidence

ORD record
ord-27d80c10d6244a83925f7c7cce729474
Source dataset
uspto-grants-2002_05
Patent number
US06391915B2

Reaction notes

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