Triethylamine → Quinoline-6-carbonitrile

HRID 1890546Notes

Reaction equation

HRID 1890546 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(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

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 11052097Quinoline-6-carboxamide

Product 1

HCID 592995Quinoline-6-carbonitrileYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of quinoline-6-carboxamide (O-3) (1.2 g, 7.2 mmol) and triethylamine (2.2 g, 21.8 mmol) in DCM (50 mL) at 0° C. was added trifluoroacetic acid anhydride (1.9 g, 8.9 mmol). The reaction was stirred for 10 mins at 0° C., then quenched with water. The resulting mixture was extracted with DCM. The organic layer was dried over anhydrous Na2SO4, and concentrated to afford the desired title compound (1.0 g). MS (m/z): 154 (M)+.

Workup

  1. customquenched with water
  2. extractionThe resulting mixture was extracted with DCM
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f97a86272d12497f9ca1ad75be26256a
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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