HCID 18380142, compound → HCID 18380146, compound

HRID 243515Notes

Reaction equation

HRID 243515 reaction equation
N[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([I:9])=[C:4]([CH3:10])[N:3]=1.N([O-])=[O:12].[Na+]>OS(O)(=O)=O.O>[CH3:8][C:7]1[C:2](=[O:12])[NH:3][C:4]([CH3:10])=[C:5]([I:9])[CH:6]=1

Participants

5

Reactant 2

HCID 18380142HCID 18380142, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 18380146HCID 18380146, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

2-Amino-3,6-dimethyl-5-iodopyridine (4.01 g, 16.2 mmol) was dissolved in 0.5 M H2SO4 (70 mL) and the resulting solution cooled to 0° C. with stirring. A solution of sodium nitrite (3.3 g, 48.0 mmol) in H2O (5 mL) was added dropwise over 10 min. at 0° C. with vigorous stirring. After 1.5 h the cooling bath was removed and the mixture warmed to r.t. over 1 h. The solid was vacuum filtered, washed with H2O (50 mL), the solids air dried and then dried under vacuum for 18 h, yielding 3.9 g (15.7 mmol, 97%) of white solid.

Workup

  1. customAfter 1.5 h the cooling bath was removed
  2. temperaturethe mixture warmed to r.t. over 1 h
  3. filtrationfiltered
  4. washwashed with H2O (50 mL)
  5. customthe solids air dried
  6. customdried under vacuum for 18 h

Sources & evidence

ORD record
ord-34657ea52c814a889cc71dcf87994135
Source dataset
uspto-grants-2014_02
Patent number
US08653248B2

Reaction notes

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