HCID 18007174, compound → HCID 18007432, compound

HRID 1351855Notes

Reaction equation

HRID 1351855 reaction equation
N[CH2:2][C:3]1([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:13][CH3:14])[CH2:6][CH2:5][CH2:4]1.N([O-])=O.[Na+]>C(O)(=O)C.O>[CH3:14][O:13][C:11]1[C:12]2[CH2:2][C:3](=[O:15])[CH2:4][CH2:5][CH2:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 18007174HCID 18007174, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 18007432HCID 18007432, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a suspension of 1-aminomethyl-1-hydroxy-8-methoxy-1,2,3,4-tetrahydronaphthalene (2.54 g) in 10% acetic acid was added dropwise a solution of sodium nitrite (1.27 g) in water (6.4 ml) under ice-cooling. The mixture was stirred at the same temperature for 2 hours and then partitioned between ethyl acetate and water. The organic layer was separated, washed with an aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (10:1) to afford 4-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-one (1.08 g).

Workup

  1. temperaturecooling
  2. custompartitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with an aqueous sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (10:1)

Sources & evidence

ORD record
ord-956b0f07ba8842e9b5c303e8825564fd
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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