Triethylamine → 2-(6-Oxo-1,6-dihydro-pyridazin-4-yloxy)-benzonitrile

HRID 2381351Notes

Reaction equation

HRID 2381351 reaction equation
[O:1]=[C:2]1[NH:7][N:6]=[CH:5][C:4]([O:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([NH2:13])=O)=[CH:3]1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[O:1]=[C:2]1[NH:7][N:6]=[CH:5][C:4]([O:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]#[N:13])=[CH:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 579191962-(6-Oxo-1,6-dihydro-pyridazin-4-yloxy)-benzamide

Product 1

HCID 579191842-(6-Oxo-1,6-dihydro-pyridazin-4-yloxy)-benzonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(6-oxo-1,6-dihydro-pyridazin-4-yloxy)-benzamide (31.1 g, 0.14 mol) in methylene chloride and triethylamine (65.5 g, 0.65 mol) was treated dropwise with trifluoroacetic anhydride (62.2 g, 0.30 mol). The resulting solution was stirred at 25° C. for 5 min. After this time, the reaction was washed with a 2N aqueous hydrochloric acid solution and a saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered, rinsed and concentrated in vacuo to afford 2-(6-oxo-1,6-dihydro-pyridazin-4-yloxy)-benzonitrile (25.1 g, 87%) as a white solid; ESI-MS 214 [M+H+]; HPLC: >95% (purity). 1H-NMR (300 MHz, CDCl3) δ 11.75 (s, 1H), 7.91 (s, 1H), 7.71-7.81 (m, 2H), 7.44-7.49 (m, 1H), 7.28-7.30 (m, 1H), 5.98 (s, 1H).

Workup

  1. washAfter this time, the reaction was washed with a 2N aqueous hydrochloric acid solution
  2. dry with materiala saturated aqueous sodium bicarbonate solution, dried over sodium sulfate
  3. filtrationfiltered
  4. washrinsed
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-11c20d7f01a444688af276aee092bbe4
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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