Hydrochloric Acid → HCID 58415338, compound

HRID 2075238Notes

Reaction equation

HRID 2075238 reaction equation
[I:1]I.[CH2:3]([C:10]1[N:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(O)(O)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].Cl>O.C1COCC1>[CH2:3]([C:10]1[N:15]=[C:14]([I:1])[C:13]([OH:16])=[CH:12][CH:11]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 767Carbonic AcidHCID 807IodineHCID 24477Sodium ThiosulfateHCID 139788063-Pyridinol, 6-(phenylmethyl)-

Product 1

HCID 58415338HCID 58415338, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Iodine (3.21 g, 12.6 mmol) was added to a solution of 6-benzylpyridin-3-ol (2.34 g, 12.6 mmol) and sodium carbonate anhydrous (1.06 mL, 25.3 mmol) in water (60 mL) and THF (60 mL). The mixture was allowed to stir for 1 h at room temperature, treated with sodium thiosulfate, and acidified pH 3 using 5M aqueous HCl. Extractive workup and flash chromatography using EtOAc/hexanes gave 6-benzyl-2-iodopyridin-3-ol. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.62 (s, 1H), 7.13-7.34 (m, 5H), 6.99-7.11 (m, 2H), 3.95 (s, 2H). MS (ESI) m/z: Calculated; 311.0 Observed: 311.9 (M++1).

Sources & evidence

ORD record
ord-3a25f0ab79404e3dbd025a1c4e10ddef
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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