Sodium hydride → HCID 18619157, compound

HRID 1862279Notes

Reaction equation

HRID 1862279 reaction equation
[H-].[Na+].Cl[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([Cl:13])[N:5]=1.[C:14]([O:18][CH3:19])(=[O:17])[CH2:15][OH:16]>O1CCCC1>[Cl:13][C:6]1[N:5]=[C:4]([O:16][CH2:15][C:14]([O:18][CH3:19])=[O:17])[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66774Methyl GlycolateHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 18619157HCID 18619157, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2.0 g of sodium hydride was added to a mixture of 9.65 g of 2,6-dichloro-3-nitropyridine, 4.95 g of methyl glycolate and 100 ml of tetrahydrofuran at 0° C. The mixture was stirred at 0° C. for 4 hours. The reaction solution was poured into ice water, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 10.86 g of 6-chloro-2-(methoxycarbonyl)methoxy-3-nitropyridine.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8245e60abb12486baf968052d1b19617
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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