Hydrochloric Acid → HCID 22379664, compound

HRID 895370Notes

Reaction equation

HRID 895370 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[I:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.[OH-].[Na+].Cl>C1(C)C=CC=CC=1>[I:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 108944-IodophenolHCID 14798Sodium HydroxideHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 22379664HCID 22379664, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Chloro-5-nitro-pyridine (60 grams, 0.38 mol) and 4-iodo-phenol (83.5 grams, 0.38 mol), 50% aqueous sodium hydroxide (475 mL) and toluene (475 mL) were added to a flask and stirred at room temperature for 2 hours. The reaction mixture was cooled to 0° C. and concentrated hydrochloric acid was added to adjust the pH to two. The aqueous layer was separated from the toluene layer and extracted with diethyl ether (3×400 mL). The diethyl ether and toluene solution were combined and washed with 1M sodium hydroxide (2×300 mL). The organic layer was concentrated under vacuum to yield 96.5 grams of crude product. This material was recrystallized from hexanes and ethyl acetate to provide 85.3 grams (66%) of the title compound. MS m/z: ESI+ 343.0 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customThe aqueous layer was separated from the toluene layer
  3. extractionextracted with diethyl ether (3×400 mL)
  4. washwashed with 1M sodium hydroxide (2×300 mL)
  5. concentrationThe organic layer was concentrated under vacuum
  6. customto yield 96.5 grams of crude product
  7. customThis material was recrystallized from hexanes and ethyl acetate

Sources & evidence

ORD record
ord-bfd34c1518e74953b04661c8637f7634
Source dataset
uspto-grants-2005_07
Patent number
US06916807B2

Reaction notes

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