Ethylene Glycol → HCID 21255107, compound

HRID 1788765Notes

Reaction equation

HRID 1788765 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:15]3[C:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)=C(C#N)[CH:8]=2)[CH:2]=1.[OH-:18].[K+].C.[CH2:21]([OH:24])[CH2:22]O>O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:15]3[C:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)=[C:22]([C:21]([OH:24])=[O:18])[CH:8]=2)[CH:2]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 297MethaneHCID 14797Potassium HydroxideHCID 11831061HCID 11831061, compound

Product 1

HCID 21255107HCID 21255107, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 3-(3-pyridyl)-5,6,7,8-tetrahydroindolizine-1-carbonitrile (15.6 g) and of potassium hydroxide powder (15.8 g) in ethylene glycol (150 cc) is heated at a temperature of about 156° C. for 11 hours and 30 minutes. After 16 hours' stirring at a temperature of about 20° C., the solvent is evaporated off under reduced pressure (2 mm Hg; 0.27 kPa) at a temperature of about 100° C. The residue obtained is dissolved in distilled water (250 cc). The solution obtained is treated with decolourising charcoal (0.5 g) and filtered. The filtrate is adjusted to a pH of about 5 at a temperature of about 25° C. by addition of a 5 N aqueous solution of hydrochloric acid (50 cc). The suspension obtained is stirred at a temperature of about 20° C. for 1 hour. The crystals are separated off by filtration, washed 5 times with distilled water (250 cc in total) and then dried in air. 3-(3-Pyridyl)-5,6,7,8-tetrahydroindolizine-1-carboxylic acid (13.4 g) is thus obtained in the form of beige crystals melting at 198° C.

Workup

  1. customthe solvent is evaporated off under reduced pressure (2 mm Hg; 0.27 kPa) at a temperature of about 100° C
  2. customThe residue obtained
  3. customThe solution obtained
  4. filtrationfiltered
  5. additionThe filtrate is adjusted to a pH of about 5 at a temperature of about 25° C. by addition of a 5 N aqueous solution of hydrochloric acid (50 cc)
  6. customThe suspension obtained
  7. stirringis stirred at a temperature of about 20° C. for 1 hour
  8. customThe crystals are separated off by filtration
  9. washwashed 5 times with distilled water (250 cc in total)
  10. customdried in air

Sources & evidence

ORD record
ord-f11982bfa30746859d2d86d97b005c43
Source dataset
uspto-grants-1987_08
Patent number
US04684658

Reaction notes

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