Iodine → N-(1,2,3,4-Tetrahydro-5-iodo-8-methoxy-2-naphthalenyl)acetamide

HRID 2058951Notes

Reaction equation

HRID 2058951 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([NH:13][C:14](=[O:16])[CH3:15])[CH2:9][CH2:8]2.C(Cl)Cl.[I:20]I>C(OC(F)(F)F)(=O)C.[Ag].O>[I:20][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:12]2[C:7]=1[CH2:8][CH2:9][CH:10]([NH:13][C:14](=[O:16])[CH3:15])[CH2:11]2

Participants

6

Reactant 3

HCID 807IodineHCID 6344Dichloromethane2×HCID 30189202-Acetamido-8-methoxytetralin

Product 1

HCID 12924802N-(1,2,3,4-Tetrahydro-5-iodo-8-methoxy-2-naphthalenyl)acetamide

Reagents, catalysts & solvents 2

HCID 88178197Silver trifluoromethyl acetateCatalystHCID 962WaterSolvent

Procedure

To a suspension of 2.19 g. (0.01 mol.) of N-(1,2,3,4-tetrahydro-8-methoxy-2-naphthalenyl) acetamide and 2.21 g (0.01 mole) of silver trifluoromethyl acetate in 80 ml. of methylene chloride was added dropwise a solution of iodine (2.52 g.; 0.02 mole) in 80 ml. of methylene chloride. The reaction mixture was stirred for one hour at room temperature, filtered and evaporated to leave an oil to which 100 ml. of water was added. After 30 minutes the oil solidified. The crystals were collected, dried and recrystallized from ethanol to give N-(1,2,3,4-tetrahydro-5-iodo-8-methoxy-2-naphthalenyl) acetamide as a white solid m.p. 202°-3°.

Workup

  1. additionTo a suspension of 2.19 g
  2. filtrationfiltered
  3. customevaporated
  4. customto leave an oil to which 100 ml
  5. waitAfter 30 minutes the oil solidified
  6. customThe crystals were collected
  7. customdried
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a267fa8a58d6483681999e9a36194431
Source dataset
uspto-grants-1982_03
Patent number
US04320148

Reaction notes

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