Water → 5-Cyanoquinoline

HRID 710477노트

반응식

HRID 710477 반응식
I[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:12]([Cu])#[N:13].[C-]#N.[Na+].O>CN(C=O)C.CCOC(C)=O>[C:12]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2)#[N:13]

참가 물질

7

반응물 4

HCID 962WaterHCID 8929Sodium CyanideHCID 220249805-IodoquinolineHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 47150285-Cyanoquinoline수율 97.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 5-iodoquinoline (0.56 g; 2.2 mmol) and CuCN (0.51 g; 5.7 mmol) in anhydrous DMF (3 ml) was refluxed for 40 min under N2. After cooling to room temperature, the mixture was diluted to 20 ml with EtOAc and NaCN (0.75 g; 15.3 mmol) was added followed by H2O (10 ml). The resulting mixture was vigorously stirred for 10 min and organic phase was separated, washed with H2O, brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness to give the title compound (0.33 g; 97%) as colourless solid. 1H-NMR (CDCl3) 7.59-7.63 (m, 1H); 7.78 (m, 1H); 7.98 (dd, 1H, J=3, 6 Hz); 8.36 (d, 1H, J=9 Hz); 8.54 (m, 1H): 9.05 (dd, 1H, J=3, 6 Hz).

후처리

  1. temperaturewas refluxed for 40 min under N2
  2. additionwas added
  3. customorganic phase was separated
  4. washwashed with H2O, brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customfiltrate evaporated to dryness

출처 및 근거

ORD 기록
ord-eac43da1968942e88acade790e4c5c29
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181182B2

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