Sodium Hydroxide → HCID 15572413, compound

HRID 443415Notes

Reaction equation

HRID 443415 reaction equation
C([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH:12]([NH:14][C:15](=O)[CH3:16])[CH3:13])=[N:9][CH:10]=1)(=O)C.[OH-].[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[CH2:15]([NH:14][CH:12]([CH3:13])[CH2:11][C:8]1[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][N:9]=1)[CH3:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15572422HCID 15572422, compound

Product 1

HCID 15572413HCID 15572413, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 0.39 g of 5-acetoxy-2-(2-acetylaminopropyl)-pyridine in 20 ml of anhydrous tetrahydrofuran, 3.6 ml of a 1 molar solution of alanetriethylamine in toluene are added dropwise while stirring at 0°. After 12 hours 22 ml of 2 N aqueous sodium hydroxide are added at 0°, and the mixture evaporated azeotropically with isopropanol. The residue is taken up in 50 ml of methanol, the pH of the solution adjusted to 8 with 5 N ethereal hydrogen chloride, the resulting salts filtered off, and the filtrate evaporated. The residue is triturated with isopropanol, to yield the 2-(2-ethylaminopropyl)-5-pyridinol melting at 75°-79°.

Workup

  1. customthe mixture evaporated azeotropically with isopropanol
  2. filtrationthe resulting salts filtered off
  3. customthe filtrate evaporated
  4. customThe residue is triturated with isopropanol

Sources & evidence

ORD record
ord-0038669ff8554b06b62206555e3fd087
Source dataset
uspto-grants-1981_04
Patent number
US04260619

Reaction notes

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