Pyridine → 6-Bromonaphthalene-2-carbonitrile

HRID 391335Notes

Reaction equation

HRID 391335 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH2:14])=O)[CH:6]=[CH:5]2.N1C=CC=CC=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]#[N:14])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 574280376-Bromo-2-naphthamide

Product 1

HCID 146621156-Bromonaphthalene-2-carbonitrileYield 70.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 6-bromo-2-naphthamide (1 g, 4.00 mmol) in dioxane (8.00 ml) at 0° C. was added pyridine (0.647 ml, 8.00 mmol) and then TFAA (0.621 ml, 4.40 mmol) dropwise. The reaction was stirred at room temperature for 3 h. The mixture was quenched with H2O and extracted with EtOAc two times, dried over magnesium sulfate, filtered, concentrated. The title compound (653 mg, 70%) was isolated as a beige solid, and used as is for the next step.

Workup

  1. customThe mixture was quenched with H2O
  2. extractionextracted with EtOAc two times
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-738b927a24984ec88ef771e83a58ff18
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

Loading…