Triethylamine → Quinoline-6-carbonitrile

HRID 449246

Reaction equation

HRID 449246 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH2:13])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 11052097Quinoline-6-carboxamide

Product 1

HCID 592995Quinoline-6-carbonitrileYield 60.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of quinoline-6-carboxamide (177 g, 1.03 mol) in chloroform (1.5 lit.) and triethylamine (520.15 g, 5.15 mol), trifluoroacetic anhydride (540.34 g, 2.57 mol) was added dropwise below 10° C. After 1.5 h, the pH was adjusted to 7 with sodium bicarbonate solution and extracted with dichloromethane. The organic layer was dried with sodium sulphate and concentrated to afford the title compound as a brown solid (96 g, 59%).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried with sodium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5c5d4f6564be47c5ab8ebc05a21d0e28
Source dataset
uspto-grants-2013_07
Patent number
US08481739B2

Linked notes

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