Phosphorus oxychloride → 4-Chloro-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbonitrile

HRID 970552ノート

反応式

HRID 970552 の反応式
C1([NH:7][C:8]([C:10]2[C:11](=[O:22])[N:12]([CH3:21])[C:13]3[C:18]([C:19]=2O)=[CH:17][CH:16]=[CH:15][CH:14]=3)=O)CCCCC1.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH3:21])[C:11](=[O:22])[C:10]=1[C:8]#[N:7]

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 54685659N-cyclohexyl-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide

生成物 1

HCID 27857484-Chloro-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbonitrile収率 82%

実験手順

A solution of Compound 2 (1.5 g, 5 mmol) in 20 mL phosphorus oxychloride was heated at 90° C. for 2 h. The solvent was evaporated under reduced pressure. The residue was suspended in ice water and neutralized by solid sodium bicarbonate. The solids formed were filtered, washed by water, and purified by flash chromatography eluting with 1% methanol in dichloromethane to yield 903 mg (82%) of white solids. M.P. 235° C. 1H NMR (DMSO-d6): 3.66 (s, 3H), 7.50 (t, J=7.7 Hz, 1H), 7.74 (d, J=8.6 Hz, 1H), 7.91 (t, J=8.7 Hz, 1H), 8.08 (d, J=7.6 Hz, 1H). EIMS m/z 219 (M+1), 241 (M+23). Anal. (C17H7ClN2O) C, H, N.

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed by water
  5. custompurified by flash chromatography
  6. washeluting with 1% methanol in dichloromethane

出典と根拠

ORDレコード
ord-c9f7cdde55954dd48c807d1d8c04a8fd
出典データセット
uspto-grants-2007_12
特許番号
US07312221B2

反応ノート

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