Water → 5-Cyanoquinoline

HRID 710477ノート

反応式

HRID 710477 の反応式
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]

参加物

7

反応物 4

HCID 962WaterHCID 8929Sodium CyanideHCID 220249805-IodoquinolineHCID 178418546HCID 178418546、化合物

生成物 1

HCID 47150285-Cyanoquinoline収率 97.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-eac43da1968942e88acade790e4c5c29
出典データセット
uspto-grants-2015_11
特許番号
US09181182B2

反応ノート

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