Iodine → HCID 58415369, compound

HRID 2075241Notes

Reaction equation

HRID 2075241 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([OH:15])[CH:11]=[N:12][C:13]=1[Cl:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:16]I>>[CH2:1]([C:8]1[CH:9]=[C:10]([OH:15])[C:11]([I:16])=[N:12][C:13]=1[Cl:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 807IodineHCID 584152845-Benzyl-6-chloropyridin-3-ol

Product 1

HCID 58415369HCID 58415369, compound

Procedure

5-benzyl-6-chloropyridin-3-ol (0.73 g, 3.3 mmol) and I2 (0.21 mL, 4.0 mmol). The mixture became homogeneous and yellow after stirring for 16 h. The mixture was washed with sodium thiosulfate (100 mL), and then treated cautiously with conc. HCl until the pH was 2 by pH paper. The solution was extracted with EtOAc (3×50 mL), and the combined organic extracts were dried over MgSO4, filtered and concentrated to afford a pale yellow solid. The solid was purified by triturating with minimal DCM and ether to give a beige solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.90-11.09 (1H, br s), 7.30-7.37 (2H, m), 7.17-7.28 (3H, m), 6.99 (1H, s), 3.95 (2H, s); MS (ESI) m/z: Calculated: 344.9; Observed: 345.9 (M++1).

Workup

  1. washThe mixture was washed with sodium thiosulfate (100 mL)
  2. additiontreated cautiously with conc. HCl until the pH was 2 by pH paper
  3. extractionThe solution was extracted with EtOAc (3×50 mL)
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a pale yellow solid
  8. customThe solid was purified
  9. customby triturating with minimal DCM and ether
  10. customto give a beige solid

Sources & evidence

ORD record
ord-6392d740a39f4325af9e9421a22fbb24
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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