Triethylamine → Quinoline-6-carbonitrile

HRID 911346

반응식

HRID 911346 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 592995Quinoline-6-carbonitrile수율 73%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-33fd24d558904523b3b4f91e87c9b34e
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022062B2

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