Hydrochloric Acid → HCID 58415404, compound

HRID 2075235Notes

Reaction equation

HRID 2075235 reaction equation
[I:1]I.[CH2:3]([C:10]1[N:15]=[C:14]([Cl:16])[C:13]([OH:17])=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+].Cl>O>[CH2:3]([C:10]1[N:15]=[C:14]([Cl:16])[C:13]([OH:17])=[C:12]([I:1])[CH:11]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 58415309HCID 58415309, compound

Product 1

HCID 58415404HCID 58415404, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Iodine (5.87 g, 23.1 mmol) was added to a solution of 6-benzyl-2-chloropyridin-3-ol (2.54 g, 11.6 mmol) in water (45 mL) containing potassium carbonate (3.20 g, 23.1 mmol). The mixture was allowed to stir for 3 h at room temperature, treated with sodium thiosulfate, and acidified to pH 2 using 12M aqueous HCl. The mixture was extracted with EtOAc. The organic phase was dried over MgSO4 and evaporated. Purification by flash chromatography using EtOAc/hexanes gave 6-benzyl-2-chloro-4-iodopyridin-3-ol. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.36 (br. s, 1H), 7.68 (s, 1H), 7.15-7.35 (m, 5H), 3.93 (s, 2H). MS (ESI) m/z: Calculated; 345.0; Observed: 345.9 (M++1).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialThe organic phase was dried over MgSO4
  3. customevaporated
  4. customPurification by flash chromatography

Sources & evidence

ORD record
ord-8e711dde1ad94af2a236f1c89e972863
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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