Sodium Carbonate → HCID 54437460, compound

HRID 1599075Notes

Reaction equation

HRID 1599075 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1>[NH2:3][C:4]1[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 104392-AminopyridineHCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 54437460HCID 54437460, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60% in oil, 1.26 g) was added to a 0° C. solution of 2-aminopyridine (2.00 g) in THF (10 ml) and the resultant mixture stirred at 0° C. for 1 h. A solution of 2-fluoronitrobenzene (2.21 ml) in THF (8 ml) was added dropwise and the resultant mixture allowed to attain rt overnight. Saturated aqueous sodium carbonate (10 ml) was added and the separated aqueous phase extracted into dichloromethane (3×10 ml). The combined organic extracts were washed with brine (20 ml), dried (MgSO4) and concentrated in vacuo. Flash column chromatography (cyclohexane: ethyl acetate; 3:1 as eluant) gave the title compound (2.23 g) as an orange/red solid.

Workup

  1. extractionthe separated aqueous phase extracted into dichloromethane (3×10 ml)
  2. washThe combined organic extracts were washed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd5909d86eca46eba19a75407fd74330
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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