Sodium hydride → HCID 178496563, compound

HRID 1387286

Reaction equation

HRID 1387286 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[N+:9]([O-:11])=[O:10].[H-].[Na+].[CH3:14][O:15][CH:16]1[CH2:21][CH2:20][CH:19]([CH2:22]Br)[CH2:18][CH2:17]1>CN(C=O)C.O>[N+:9]([C:3]1[C:4](=[O:8])[N:5]([CH2:22][C@H:19]2[CH2:20][CH2:21][C@@H:16]([O:15][CH3:14])[CH2:17][CH2:18]2)[CH:6]=[CH:7][C:2]=1[CH3:1])([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 3453702-Hydroxy-4-methyl-3-nitropyridineHCID 217065291-(Bromomethyl)-4-methoxycyclohexane

Product 1

HCID 178496563HCID 178496563, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 4-methyl-3-nitro-2-pyridone (0.93 g, 6.0 mmol) and sodium hydride (60% in oil, 0.25 g, 6.3 mmol) in DMF (20 mL) was stirred at rt for 1 hour. 4-Methoxycyclohexylmethylbromide (1.5 g, 7.2 mmol) in DMF (5 mL) was added. After 60 hours, the mixture was diluted with water, and extracted with ethyl acetate. The organic phase was washed, dried (MgSO4), and evaporated. Chromatography of the residue over silica gel (ethyl acetate/hexane 1/1 to 3/1) gave cis-3-nitro-1-(4-methoxycyclohexylmethyl)-4-methyl-2-pyridone which crystallized from ethyl acetate/hexane (0.16 g, 10%) and trans-3-nitro-1-(4-methoxycyclohexylmethyl)-4-methyl-2-pyridone which crystallized from ethyl acetate/hexane (0.18 g, 11%).

Workup

  1. waitAfter 60 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-d272303c95c445ac94ba1a9841d53fbb
Source dataset
uspto-grants-2001_07
Patent number
US06268365B1

Linked notes

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