2-Methoxy-3-amino-5-ethyl-6-methylpyridine → 2-Methoxy-3-hydroxy-5-ethyl-6-methylpyridine

HRID 1033007Notes

Reaction equation

HRID 1033007 reaction equation
[CH3:1][O:2][C:3]1[C:8](N)=[CH:7][C:6]([CH2:10][CH3:11])=[C:5]([CH3:12])[N:4]=1.N([O-])=[O:14].[Na+]>S(=O)(=O)(O)O.O>[CH3:1][O:2][C:3]1[C:8]([OH:14])=[CH:7][C:6]([CH2:10][CH3:11])=[C:5]([CH3:12])[N:4]=1

Participants

5

Reactant 2

HCID 103747942-Methoxy-3-amino-5-ethyl-6-methylpyridineHCID 23668193Sodium Nitrite

Product 1

HCID 118194042-Methoxy-3-hydroxy-5-ethyl-6-methylpyridineYield 43.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
110 °C

Procedure

A batch of 2-methoxy-3-amino-5-ethyl-6-methylpyridine (171 mg, 1.05 mmol) was dissolved in 5% aqueous sulfuric acid (4 mL), cooled in an ice bath, then a solution of sodium nitrite (78 mg, 1.13 mmol) in water (1 mL) was added dropwise. After 0.5 hour, the resulting mixture was added dropwise to 5% aqueous sulfuric acid (6 mL) warmed at 110° C. The solution was stirred for 0.5 hour, cooled and the product extracted into chloroform, then dried (Na2SO4), filtered and evaporated to yield 77 mg (43%) of product.

Workup

  1. temperaturecooled in an ice bath
  2. temperaturecooled
  3. extractionthe product extracted into chloroform
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-060a759a8a0c431abe55c2510f01cc0f
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

Loading…