p-Fluoronitrobenzene → HCID 86695865, compound

HRID 338752Notes

Reaction equation

HRID 338752 reaction equation
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[N:9][CH:10]=2)[CH2:5][CH2:4][NH:3]1.F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([N:9]2[CH2:8][CH2:7][C:6]3[C:11](=[CH:2][N:3]=[CH:4][CH:5]=3)[CH2:10]2)=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 569657841,2,3,4-Tetrahydro-2,7-naphthyridine--hydrogen chloride (1/1)

Product 1

HCID 86695865HCID 86695865, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Commercially available 1,2,3,4-tetrahydro-2,7-naphthyridine hydrochloride (14.5 g; 0.085 moles), 4-fluoronitrobenzene (18.0 g; 0.13 moles) and potassium carbonate (37.5 g, 0.27 moles) in anhydrous DMF (100 mL) were heated at 80° C. for 18 hours, cooled and partitioned between ethyl acetate (500 mL) and water (1 L). The layers were separated and the aqueous layer re-extracted with ethyl acetate (300 mL). The combined organic layers were washed with water (400 mL), brine, dried over sodium sulfate and evaporated in vacuo. Chromatography of the residue on silica (250 g) eluting with 20% ethyl acetate in DCM then 7.5% methanol in ethyl acetate gave the title compound (15 g) as an orange solid.

Workup

  1. temperaturecooled
  2. custompartitioned between ethyl acetate (500 mL) and water (1 L)
  3. customThe layers were separated
  4. extractionthe aqueous layer re-extracted with ethyl acetate (300 mL)
  5. washThe combined organic layers were washed with water (400 mL), brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. washChromatography of the residue on silica (250 g) eluting with 20% ethyl acetate in DCM

Sources & evidence

ORD record
ord-60224e2c52fe499d80a5eee01496dc1f
Source dataset
uspto-grants-2014_11
Patent number
US08889870B2

Reaction notes

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