Iodine → 5-Iodo-6-methylpyridin-2-amine

HRID 2227164Notes

Reaction equation

HRID 2227164 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.[I:9](O)(=O)(=O)=O.II.S(=O)(=O)(O)O.S(=O)(O)[O-].[Na+]>O.C(O)(=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([I:9])=[C:4]([CH3:8])[N:3]=1

Participants

8

Reactant 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 157652-Amino-6-methylpyridineHCID 65185Metaperiodic acidHCID 23665763Sodium Bisulfite

Product 1

HCID 9596135-Iodo-6-methylpyridin-2-amineYield 161.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 2-amino-6-picoline (5.40 g), periodic acid (2.28 g), and iodine (5.00 g) is heated in a solution of acetic acid (30 mL), water (6 mL), and sulfuric acid (0.9 mL) at 80° C. for 3 h. The reaction is cooled to room temperature and poured into 100 mL 10% aqueous sodium bisulfite. The aqueous solution is extracted with diethyl ether (3×100 mL). The combined organics are washed with 10% NaOH, then dried over Na2SO4, filtered, and concentrated. Purification by chromatography (eluent EtOAc) affords a yellow liquid. The liquid is further dried on the vacuum pump where it crystallizes to afford 2-amino-5-iodo-6-picoline (4.48 g, 38%). Physical characteristics are as follows: 1H NMR (300 MHz, DMSO-d6) δ 7.60, 6.09, 6.05, 2.38.

Workup

  1. extractionThe aqueous solution is extracted with diethyl ether (3×100 mL)
  2. washThe combined organics are washed with 10% NaOH
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by chromatography (eluent EtOAc)
  7. customaffords a yellow liquid
  8. customThe liquid is further dried on the vacuum pump where it
  9. customcrystallizes

Sources & evidence

ORD record
ord-6c25de1ddb0e4ccda6f8d6df6ca1d695
Source dataset
uspto-grants-2002_07
Patent number
US06413958B2

Reaction notes

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