3-Hydroxypyridine → HCID 21558649, compound

HRID 1578715Notes

Reaction equation

HRID 1578715 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br>CS(C)=O>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:3][C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 123681,6-DibromohexaneHCID 24758Sodium hydride

Product 1

HCID 21558649HCID 21558649, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (1.32g.) was added portionwise under an atmosphere of nitrogen during 30 minutes, to a stirred solution of 3-hydroxypyridine (2.85g.) in dry dimethylsulphoxide (28ml.) cooled to below 25°C. When reaction ceased, 1,6-dibromohexane (3.66g.) was added dropwise with stirring and cooling, and the resulting mixture was stirred a further 31/2 hours. The mixture was poured into ice-water, and the precipitated product was filtered off and crystallised from petroleum ether (b.p.60°- 80°C.), to give 1,6-bis-pyrid-3-yloxyhexane, m.p. 85°C.

Workup

  1. temperaturecooled to below 25°C
  2. customWhen reaction
  3. temperaturecooling
  4. stirringthe resulting mixture was stirred a further 31/2 hours
  5. filtrationthe precipitated product was filtered off
  6. customcrystallised from petroleum ether (b.p.60°- 80°C.)

Sources & evidence

ORD record
ord-a01c32ed205d4713b9efe399a8c93c8b
Source dataset
uspto-grants-1976_02
Patent number
US03939169

Reaction notes

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