HCID 12262631, compound → 91495-63-5

HRID 274079Notes

Reaction equation

HRID 274079 reaction equation
N[CH2:2][C:3]1([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH2:6][CH2:5][CH2:4]1.N([O-])=O.[Na+]>C(O)(=O)C.O>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]2[CH2:6][CH2:5][CH2:4][C:3](=[O:15])[CH2:2][C:12]=2[CH:11]=1

Participants

5

Reactant 2

HCID 12262631HCID 12262631, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 1055957491495-63-5Yield 76.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 1-aminomethyl-7-methoxy-1,2,3,4-tetrahydro-1-naphthalenol (27.50 g) in 10% aqueous acetic acid solution (250 ml) was added dropwise a solution of sodium nitrite (10.07 g) in water (61 ml) at 8° C.~9° C. The reaction mixture was stirred for 2 hours at the same temperature. The resulting precipitates were collected by filtration. The precipitates were dissolved in ethyl acetate. The solution was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography (silica gel, n-hexane:ethyl acetate:chloroform=5:1:3) to give 3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-one (19.39 g) as a white powder.

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. dissolutionThe precipitates were dissolved in ethyl acetate
  4. dry with materialThe solution was dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, n-hexane:ethyl acetate:chloroform=5:1:3)

Sources & evidence

ORD record
ord-9dda68e7336240aaa16a72cc41678acc
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

Loading…