Water → 2-Amino-3-(4-chlorobutyloxy)pyridine

HRID 357015Notes

Reaction equation

HRID 357015 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][N:5]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15][Cl:16].O>CS(C)=O>[NH2:3][C:4]1[C:9]([O:10][CH2:12][CH2:13][CH2:14][CH2:15][Cl:16])=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 281142-Amino-3-HydroxypyridineHCID 813641-Bromo-4-chlorobutane

Product 1

HCID 189367812-Amino-3-(4-chlorobutyloxy)pyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of 20 g (500 mmol) of 60% oily sodium hydride in 500 ml of dimethyl sulfoxide, 55.06 g (500 mmol) of 2-amino-3-hydroxypyridine was added at room temperature, followed by stirring for 15 minutes. To this mixture, 57.62 ml (500 mmol) of 1-bromo-4-chlorobutane was added, followed by stirring at 80° C. for 3 hours. After cooling, the reaction mixture was poured into water, extracted with ethyl acetate, washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent: n-hexane/ethyl acetate=1/1→1/4→1/9). The resulting crude crystal was purified by recrystallization (solvent: chloroform-diethyl ether) to yield 10.35 g (10.3%, white crystal) of the desired product.

Workup

  1. additionwas added at room temperature
  2. stirringby stirring at 80° C. for 3 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washwashed with water
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent: n-hexane/ethyl acetate=1/1→1/4→1/9)
  9. customThe resulting crude crystal was purified by recrystallization (solvent: chloroform-diethyl ether)

Sources & evidence

ORD record
ord-1882b61a0ead4f9e9b96bf8ea578d82f
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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