Phosphorus oxychloride → 4-Chloro-7-methylquinoline-2-carbonitrile

HRID 2422535ノート

反応式

HRID 2422535 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[N+:9]([O-])[C:8]([C:13]#[N:14])=[CH:7][CH:6]=2.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:6]1[C:5]2[C:10](=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:9]=[C:8]([C:13]#[N:14])[CH:7]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 667907327-Methylquinoline-2-carbonitrile 1-oxide

生成物 1

HCID 597749194-Chloro-7-methylquinoline-2-carbonitrile

反応条件

温度
100 °C

実験手順

A mixture of 7-methylquinoline-2-carbonitrile 1-oxide (11.5 g, 63 mmol) and phosphorus oxychloride (47 mL, 500 mmol) was heated at 100° C. for 10 min then at 200° C. for 20 min. The reaction mixture was poured into crushed ice and the precipitate was filtered. The crude material was then purified by flash chromatography on silica gel (eluting solvent: 3% acetone in dichloromethane) to provide the title compound. 1HNMR (400 MHz, acetone-d6): δ 8.25 (d, 1H), 8.10 (s, 1H), 8.00 (d, 1H), 7.82 (dd, 1H), 2.65 (s, 3H).

後処理

  1. additionThe reaction mixture was poured
  2. custominto crushed ice
  3. filtrationthe precipitate was filtered
  4. customThe crude material was then purified by flash chromatography on silica gel (eluting solvent: 3% acetone in dichloromethane)

出典と根拠

ORDレコード
ord-214f58c58b894c908e413bc793447d6b
出典データセット
uspto-grants-2011_06
特許番号
US07960409B2

反応ノート

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