Triethylamine → Quinoline-6-carbonitrile

HRID 2041234Notes

Reaction equation

HRID 2041234 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 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 6-quinolinecarboxamide (1.5 g, 8.95 mmol) in DCM (50 mL), add triethylamine (2.7 g, 26.8 mmol) and cool the reaction mixture to 0° C. Add trifluoroacetic acid anhydride (2.4 g, 11.16 mmol) to the reaction mixture and stir for 10 min at 0° C. Quench the reaction mixture with water (20 mL) and separate the organic layer. Extract aqueous layer with DCM (2×15 mL). Combine the organic extracts and dry over anhydrous Na2SO4. Evaporate the solvent to obtain the desired intermediate as a white solid (1.0 g, 73%). GC-MS m/z: 154 (M+).

Workup

  1. customQuench the reaction mixture with water (20 mL)
  2. customseparate the organic layer
  3. dry with materialCombine the organic extracts and dry over anhydrous Na2SO4
  4. customEvaporate the solvent

Sources & evidence

ORD record
ord-0f3334b3ccbc4101a47508983ee7d4cc
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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