Acetic Anhydride → 2-Hydroxymethyl-3-methyl-4-(2-morpholinoethylthio)pyridine

HRID 52137Notes

Reaction equation

HRID 52137 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([S:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:5]=[CH:4][N+:3]=1[O-].C(OC(=O)C)(=[O:21])C>>[OH:21][CH2:1][C:2]1[C:7]([CH3:8])=[C:6]([S:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 199631002,3-dimethyl-4-(2-morpholinoethylthio)pyridine-N-oxide

Product 1

HCID 199630392-Hydroxymethyl-3-methyl-4-(2-morpholinoethylthio)pyridine

Conditions

Temperature
90 °C

Procedure

2,3-Dimethyl-4-(2-morpholinoethylthio)pyridine-N-oxide (3.0 g) was dissolved in acetic anhydride (30 ml) and the mixture was stirred at 90° C. for 1.5 hours. The solvent was distilled away and water was added to the residue. The mixture was extracted with chloroform and dried over anhydrous magnesium sulfate, and the solvent was distilled away. The residual 2-acetoxymethyl-3-methyl-4-(2-morpholinoethylthio)pyridine (3.2 g) was dissolved in methanol (30 ml) and thereto was added sodium hydroxide (0.88 g) in water (10 ml) under ice-cooling. The mixture was stirred under ice-cooling for 1.5 hours and at room temperature for 2 hours. After the completion of the reaction, the methanol was distilled away and the residue was extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and the solvent was distilled away to give 2.1 g of 2-hydroxymethyl-3-methyl-4-(2-morpholinoethylthio)pyridine.

Workup

  1. distillationThe solvent was distilled away
  2. additionwater was added to the residue
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away
  6. dissolutionThe residual 2-acetoxymethyl-3-methyl-4-(2-morpholinoethylthio)pyridine (3.2 g) was dissolved in methanol (30 ml)
  7. additionwas added sodium hydroxide (0.88 g) in water (10 ml) under ice-
  8. temperaturecooling
  9. stirringThe mixture was stirred under ice-
  10. temperaturecooling for 1.5 hours and at room temperature for 2 hours
  11. customAfter the completion of the reaction
  12. distillationthe methanol was distilled away
  13. extractionthe residue was extracted with chloroform
  14. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  15. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-a98d48cb55634b7c9ce2564585732987
Source dataset
uspto-grants-1997_04
Patent number
US05616581

Reaction notes

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