Sodium Cyanide → 6-(4-Chloro-3-methoxy-phenyl)-2,2-dimethyl-3,6-dioxo-5-pyridin-4-yl-hexanenitrile

HRID 2223097ノート

反応式

HRID 2223097 の反応式
[CH3:1][C:2]([CH3:15])([C:5](=[O:14])[CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)[C:3]#[N:4].[C-]#N.[Na+].[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][C:21]=1[O:28][CH3:29].C(=O)([O-])O.[Na+]>CN(C=O)C.O>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([C:24](=[O:25])[CH:7]([C:8]2[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=2)[CH2:6][C:5](=[O:14])[C:2]([CH3:15])([CH3:1])[C:3]#[N:4])=[CH:22][C:21]=1[O:28][CH3:29]

参加物

7

反応物 4

HCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 129097254-Chloro-3-methoxybenzaldehydeHCID 691376492,2-Dimethyl-3-oxo-5-pyridin-4-yl-pent-4-enenitrile

生成物 1

HCID 691376796-(4-Chloro-3-methoxy-phenyl)-2,2-dimethyl-3,6-dioxo-5-pyridin-4-yl-hexanenitrile収率 222.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒3 回

実験手順

A solution of the product of Example 1 Step 1 (4.0 g, 20.0 mmol) in DMF (7 ml) was added to a solution of sodium cyanide (300 mg, 6.12 mmol) in DMF (7 ml) over 15 minutes at room temperature. After stirring for a further 15 minutes, a solution of 4-chloro-3-methoxy-benzaldehyde (F. Claudi et al., J. Med. Chem., 1992, 35, 4408) (640 mg, 3.75 mmol) in DMF (6 ml) was added dropwise. The mixture was stirred at room temperature for 18 hours and then diluted with water and the pH of the solution adjusted to 9 with aqueous sodium hydrogen carbonate solution. The mixture was extracted with chloroform and the organic phase washed with water and brine, dried and concentrated in vacuo. The residue was chromatographed on silica gel eluting with chloroform/ethanol/0.880 ammonia solution (90:9:1) to give the title compound (3.1 g, 42%); MS (ES+) m/e 371, 373 [M+H]+.

後処理

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. extractionThe mixture was extracted with chloroform
  3. washthe organic phase washed with water and brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with chloroform/ethanol/0.880 ammonia solution (90:9:1)

出典と根拠

ORDレコード
ord-b8606eb0ae104e2294f4aee316cf6d52
出典データセット
uspto-grants-2008_05
特許番号
US07375105B2

反応ノート

読み込み中…