1-Bromooctane → HCID 19969073, compound

HRID 1492895Notes

Reaction equation

HRID 1492895 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.[CH2:10](Br)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(OCC)(=O)C>CN(C)C=O.[Cl-].[Na+].O>[CH2:10]([N:7]1[CH:8]=[CH:9][C:4](=[O:3])[CH:5]=[CH:6]1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 81401-BromooctaneHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 178418642HCID 178418642, compound

Product 1

HCID 19969073HCID 19969073, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of sodium hydride (2.04 g) in N,N-dimethylformamide (50 ml) was added 4-hydroxypyridine (5 g) at room temperature. Octyl bromide (9.08 ml) was added thereto. The mixture was stirred for 2 hours at 50° C. The reaction mixture was added to a mixture of brine (100 ml), trtrahydrofuran (100 ml) and ethyl acetate (100 ml). The organic layer was separated and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give 1-octyl-4-pyridone (14.7 g).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe magnesium sulfate was filtered off
  4. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-52b356c1bab84cb98eb057737198dab7
Source dataset
uspto-grants-1994_12
Patent number
US05376634

Reaction notes

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