HCID 18007174, compound → HCID 18007432, compound

HRID 2299641Notes

Reaction equation

HRID 2299641 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 l-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-d1ec2419733c4d588735eceee4b238b4
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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