Pyrrolidine → HCID 178427996, compound

HRID 1764102Notes

Reaction equation

HRID 1764102 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[C:7](Cl)[CH:6]=[C:5]([CH3:10])[N+:4]=1[O-:11].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>O>[NH2:2][C:3]1[CH:8]=[C:7]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:6]=[C:5]([CH3:10])[N+:4]=1[O-:11]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 178426121HCID 178426121, compound

Product 1

HCID 178427996HCID 178427996, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
155 °C

Procedure

A quantity (1.95 g., 0.01 mole) of 2-amino-4-chloro-6-methylpyridine-1-oxide hydrochloride (prepared in Part B, Example 1, above) with 10 ml. pyrrolidine and 10 ml. water was sealed in a reinforced bottle and heated in an oil bath at the temperature 155° C. for 5 hrs. After cooling, this reaction mixture was diluted with water and extracted with three 50-ml. portions of methylene chloride. The methylene chloride extract was dried over anhydrous sodium sulfate, treated with charcoal, and filtered. The methylene chloride was removed from the filtrate by evaporation under reduced pressure, and the residue thus obtained was triturated with acetone and collected on a filter. The solids on the filter were crystallized from about 400 ml. acetonitrile. There was thus obtained 0.98 g. (51% yield) of 2-amino-6-methyl-4-pyrrolidinylpyridine-1-oxide as fine white needles having a melting point at 282° C. (with decomposition). The crystals became pink colored after exposure to light for several days.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with three 50-ml
  3. extractionThe methylene chloride extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. additiontreated with charcoal
  6. filtrationfiltered
  7. customThe methylene chloride was removed from the filtrate by evaporation under reduced pressure
  8. customthe residue thus obtained
  9. customwas triturated with acetone
  10. customcollected on a filter
  11. customThe solids on the filter were crystallized from about 400 ml

Sources & evidence

ORD record
ord-1a4a916682134a2aad34524eea9d0c41
Source dataset
uspto-grants-1978_09
Patent number
US04115396

Reaction notes

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