Water → 2-Chloro-6-ethoxypyridin-4-amine

HRID 1364549Notes

Reaction equation

HRID 1364549 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[O-:10][CH2:11][CH3:12].[Na+].O>C(O)C>[Cl:9][C:4]1[CH:5]=[C:6]([NH2:8])[CH:7]=[C:2]([O:10][CH2:11][CH3:12])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1376524-Amino-2,6-dichloropyridineHCID 2723922Sodium ethoxide

Product 1

HCID 534852242-Chloro-6-ethoxypyridin-4-amineYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

To 2,6-dichloro-pyridin-4-ylamine (1.08 g, 6.6 mmol) in ethanol (1.5 mL) was added sodium ethoxide (2.5 M, 2.7 mL, 6.6 mmol) and the mixture was heated in a sealed tube at 150° C. for 6 h. Water was added, and the mixture was extracted with ethyl acetate. The extracts were concentrated and purified by silica gel flash column eluting with 30% ethyl acetate in hexanes to give the titled compound (1.0 g, 88%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe extracts were concentrated
  3. custompurified by silica gel flash column
  4. washeluting with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c856fa0595ef49c887e79a9191197a6f
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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