3-Hydroxypyridine → HCID 14547287, compound

HRID 1289602Notes

Reaction equation

HRID 1289602 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:11][CH2:12][CH2:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24]>CN(C=O)C.O>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:1][CH2:11][CH2:12][CH2:13][N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])[CH:3]=1

Participants

6

Reactant 3

HCID 79713-HydroxypyridineHCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydride

Product 1

HCID 14547287HCID 14547287, compoundYield 102.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-Hydroxypyridine(2.83 g, 29.83 mmol) was dissolved in DMF (70 mL), the solution was cooled in an ice bath, NaH (1.3 g, 32.81 mmol) and N-(3-bromopropyl)phthalimide (8 g, 29.83 mmol, Aldrich) were added, the ice bath was removed, and the reaction mixture was stirred for 64 hours. The reaction was diluted with CH2Cl2 and filtered through celite to give a 1:1 mixture of N- and O-alkylated products. Recrystallization from EtOH afforded a 4:1 mixture of N- and O-alkylated products. The mother liquor was taken up in water and extracted with CH2Cl2, then the organic layer washed with water (5x) to afford the desired N-(3-(3-pyridyloxy)propyl)phthalimide (8.6 g).

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. customthe ice bath was removed
  3. additionThe reaction was diluted with CH2Cl2
  4. filtrationfiltered through celite
  5. customto give
  6. additiona 1:1 mixture of N- and O-alkylated products
  7. customRecrystallization from EtOH
  8. customafforded
  9. additiona 4:1 mixture of N- and O-alkylated products
  10. extractionextracted with CH2Cl2
  11. washthe organic layer washed with water (5x)

Sources & evidence

ORD record
ord-44c2cff947c8445ab33e7abbbc781858
Source dataset
uspto-grants-1998_05
Patent number
US05750510

Reaction notes

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