Hydrochloric Acid → HCID 57667811, compound

HRID 2191622Notes

Reaction equation

HRID 2191622 reaction equation
Cl.N[C:3]1[CH:11]=[C:10]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].N([O-])=O.[Na+].[I-:24].[K+]>O.C(O)(=O)C>[I:24][C:3]1[CH:11]=[C:10]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 57667844HCID 57667844, compound

Product 1

HCID 57667811HCID 57667811, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

To a suspension of acetic acid 17 mL, water 17 mL and hydrochloric acid 2.1 mL of 2-amino-4-phenethylbenzoic acid 1.7 g, was added water 3.0 mL solution of sodium nitrite 0.58 g at 4° C., and it was stirred at same temperature for 15 minutes. The reaction mixture was added to water 20 mL solution of potassium iodide 2.3 g at 4° C., and it was stirred at room temperature for 30 minutes. The solvent was removed under reduced pressure, and ethyl acetate was added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after sequential washing with 5% sodium thiosulfate aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate:acetic acid=66:33:1] to give 2-iodo-4-phenethylbenzoic acid 1.5 g of yellow solid.

Workup

  1. stirringit was stirred at room temperature for 30 minutes
  2. customThe solvent was removed under reduced pressure, and ethyl acetate
  3. additionwas added to it
  4. customThe organic layer was separated
  5. customcollected
  6. dry with materialdried over anhydrous magnesium sulfate
  7. washafter sequential washing with 5% sodium thiosulfate aqueous solution and saturated sodium chloride aqueous solution
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6f287ac1726e460da54e645ecfb45e5d
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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