Phosphorus oxychloride → 1-Chloro-4-methylisoquinoline

HRID 1852211ノート

反応式

HRID 1852211 の反応式
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N+:4]([O-])[CH:3]=1.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([CH3:1])=[CH:3][N:4]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 229588294-Methylisoquinoline 2-oxide

生成物 1

HCID 222502291-Chloro-4-methylisoquinoline収率 18.75%

実験手順

A solution of 4-methylisoquinoline 2-oxide (0.65 g, 4.08 mmol) in POCl3 (6 ml) was refluxed for 18 h. The solvent was evaporated under reduced pressure and the residue was diluted with cold water. The aqueous solution was basified with solid sodium carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (10% ethyl acetate in pet ether) to get desired compound (0.17 g, 18.75%) as oil. 1H NMR (400 MHz, DMSO-d6): δ ppm 8.14-8.12 (d, J=8 Hz, 1H), 7.97 (s, 1H), 7.95-7.93 (d, J=8 Hz, 1H), 7.86 (t, J=4 Hz, 1H), 7.84(t, J=8 Hz, 1H), 2.59 (s, 3H); MS: MS m/z 178.2 (M++1).

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with cold water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto get crude compound
  8. customThe crude compound was purified by silica gel chromatography (10% ethyl acetate in pet ether)

出典と根拠

ORDレコード
ord-2e033a9ccd0442bc90b915fc9e3bd29f
出典データセット
uspto-grants-2015_02
特許番号
US08957203B2

反応ノート

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