Potassium Iodide → HCID 18536110, compound

HRID 2099594Notes

Reaction equation

HRID 2099594 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2N)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N([O-])=O.[Na+].[I-:24].[K+]>Cl.O.O1CCCC1>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[I:24])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 4875Potassium IodideHCID 18433613HCID 18433613, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 18536110HCID 18536110, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-benzyloxy-naphthalen-1-ylamine (6.98 g, 28.02 mmol) in concentrated hydrogen chloride (30 mL), water (30 mL) and tetrahydrofuran (30 mL) is cooled with an ice-salt (sodium chloride) bath. A solution of sodium nitrite (2.32 g, 33.6 mmol) in water (20 mL) is then added in a dropwise manner over a 15-minute period of time and the reaction temperature is kept under 5° C. The mixture is stirred for another 30 minutes before potassium iodide (9.3 g, 56.04 mmol) in water (30 mL) is added. The resulting mixture is stirred for three hours at room temperature before being extracted with ethyl acetate, dried over sodium sulfate, filtered, concentrated and purified by silica gel chromatography (Hexanes/CH2Cl2 =25/1-20/1) to give 7-benzyloxy-1-iodo-naphthalene (6.26 g, 61%); MS m/z (M+Na+) 361.00.

Workup

  1. customis kept under 5° C
  2. additionis added
  3. extractionbefore being extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (Hexanes/CH2Cl2 =25/1-20/1)

Sources & evidence

ORD record
ord-ef81952d929947b1b1abad8b60ebd145
Source dataset
uspto-grants-2009_08
Patent number
US07569593B2

Reaction notes

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