Ammonia → 2-(2-Iodo-4-methoxyphenyl)-6-methoxy-1,2,3,4-tetrahydronaphthalene

HRID 1434116Notes

Reaction equation

HRID 1434116 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=3)[CH2:11]2)=[C:7](N)[CH:8]=1.S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:31].[K+].[I-].N>O.C(O)(=O)C>[I:31][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=2)[CH2:11]1

Participants

9

Reactant 6

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 30165Iodide IonHCID 230872055-Methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamineHCID 23668193Sodium Nitrite

Product 1

HCID 230875592-(2-Iodo-4-methoxyphenyl)-6-methoxy-1,2,3,4-tetrahydronaphthaleneYield 44.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

The title compound was synthesized by referring to J. Org. Chem., 1984, 49, 296. To 5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamine (5.0 g) was added dropwise acetic acid (50 ml) and concentrated sulfuric acid (2 ml) over 30 minutes on an ice bath, a solution of sodium nitrite (1.3 g) in water (20 ml) was then added thereto followed by stirring for 30 minutes. A solution of potassium iodide (3.5 g) and iodide (2.7 g) in water (30 ml) was added dropwise thereto over 30 minutes followed by stirring for 3 hours at room temperature. The reaction solution was neutralized with ammonia solution and a saturated aqueous solution of sodium carbonate on an ice bath, extracted with ethyl acetate, then sequentially washed with an aqueous solution of sodium thiosulfate, water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (3.1 g).

Workup

  1. customThe title compound was synthesized
  2. waitover 30 minutes followed
  3. stirringby stirring for 3 hours at room temperature
  4. extractiona saturated aqueous solution of sodium carbonate on an ice bath, extracted with ethyl acetate
  5. washsequentially washed with an aqueous solution of sodium thiosulfate, water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated in vacuo
  8. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-c451ba0dc0af4ae5b57f2872260cd3e0
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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