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

HRID 2423874Notes

Reaction equation

HRID 2423874 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 minuntes 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. stirringby stirring for 3 hours at room temperature
  3. extractiona saturated aqueous solution of sodium carbonate on an ice bath, extracted with ethyl acetate
  4. washsequentially washed with an aqueous solution of sodium thiosulfate, water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-56126ede0a80416a928d6550f2411214
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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