Isopropanol → HCID 20190405, compound

HRID 1788768Notes

Reaction equation

HRID 1788768 reaction equation
[C:1]([N:9]1[CH2:16][CH:15]([OH:17])[CH2:14][C@H:10]1[C:11](O)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C(OC(=O)C)(=O)C.[OH-].[Na+].[CH:27](O)(C)C.ClC(=C)[C:33]#[N:34]>>[OH:17][CH:15]1[CH2:16][N:9]2[C:10](=[C:11]([C:33]#[N:34])[CH:27]=[C:1]2[C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[CH2:14]1

Participants

6

Reactant 5

HCID 3776IsopropanolHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 701982-ChloroacrylonitrileHCID 53708519HCID 53708519, compound

Product 1

HCID 20190405HCID 20190405, compound

Conditions

Temperature
20 °C

Procedure

A suspension of N-nicotinoyl-4-hydroxyproline (34 g) in a mixture of 2-chloroacrylonitrile (115 cc) and of acetic anhydride (150 cc) is heated at a temperature of about 90° C. for 3 hours and 40 minutes. The solution obtained is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 70° C. The residue obtained is suspended in a 5 N aqueous solution of sodium hydroxide (500 cc) and the resulting suspension is extracted 4 times with ethyl acetate (1,250 cc in total). The organic extracts are combined, washed 4 times with distilled water (1,000 cc in total), dried over anhydrous magnesium sulphate, treated with decolourising charcoal (0.5 g), filtered and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 60° C. A crude product (13 g) is thus obtained, which is dissolved in boiling isopropanol (130 cc). The solution obtained is filtered hot and the filtrate is cooled at a temperature of about 20° C. for 2 hours. The crystals which have appeared are separated off by filtration, washed twice with isopropanol (50 cc in total) and 3 times with diethyl ether (150 cc in total), and then dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. in the presence of potassium hydroxide pellets. 2-Hydroxy-5-(3-pyridyl)-2,3-dihydro-1H-pyrrolizine-7-carbonitrile (5.6 g) is thus obtained in the form of beige crystals melting at 190° C.

Workup

  1. customThe solution obtained
  2. concentrationis concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 70° C
  3. customThe residue obtained
  4. extractionthe resulting suspension is extracted 4 times with ethyl acetate (1,250 cc in total)
  5. washwashed 4 times with distilled water (1,000 cc in total)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. additiontreated with decolourising charcoal (0.5 g)
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 60° C
  10. customA crude product (13 g) is thus obtained
  11. dissolutionwhich is dissolved
  12. customThe solution obtained
  13. filtrationis filtered hot
  14. customThe crystals which have appeared are separated off by filtration
  15. washwashed twice with isopropanol (50 cc in total) and 3 times with diethyl ether (150 cc in total)
  16. dry with materialdried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. in the presence of potassium hydroxide pellets

Sources & evidence

ORD record
ord-824e7f9651f240e689a69529a68f3509
Source dataset
uspto-grants-1987_08
Patent number
US04684658

Reaction notes

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