Sodium Hydroxide → 2-Butoxy-6-methylpyridin-4-amine

HRID 2192997Notes

Reaction equation

HRID 2192997 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[OH-:10].[Na+]>C(O)CCC.O>[CH2:9]([O:10][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:9])[N:3]=1)[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 126437072-Chloro-6-methylpyridin-4-amine

Product 1

HCID 593754742-Butoxy-6-methylpyridin-4-amine

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

2-chloro-6-methylpyridin-4-amine (36 g, 0.25 mol) and sodium hydroxide (24 g, 1 mol) were dissolved in 1-butanol (400 mL). The solution was heated at reflux for 10 h, and then cooled to rt. The reaction mixture was diluted with water (300 mL) and then extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with brine (500 mL), dried over sodium sulfate, and concentrated to afford 2-butoxy-6-methylpyridin-4-amine. 1H NMR (400 MHz, CDCl3) δ 6.05 (d, J=0.6 Hz, 1H), 5.75 (d, J=0.6 Hz, 1H), 4.18 (t, J=6.4 Hz, 1H), 2.30 (s, 3H), 1.71 (m, 2H), 1.48 (m, 2H), 0.98 (t, J=7.6 Hz, 3H). LRMS calc'd for (C10H16N2O) [M+H]+, 181; found 181.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 10 h
  3. extractionextracted with ethyl acetate (3×500 mL)
  4. washThe combined organic layers were washed with brine (500 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c6dd2203070646789140481cdaf85526
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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