Phosphorus oxychloride → 2-Chloro-5-fluoroquinoline-3-carbonitrile

HRID 1848634ノート

反応式

HRID 1848634 の反応式
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:13]#[N:14])[C:6](=O)[NH:7]2.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:6]1[C:5]([C:13]#[N:14])=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[F:1])[N:7]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 686018505-Fluoro-2-oxo-1,2-dihydro-quinoline-3-carbonitrile

生成物 1

HCID 593703262-Chloro-5-fluoroquinoline-3-carbonitrile

実験手順

5-Fluoro-2-oxo-1,2-dihydro-quinoline-3-carbonitrile (0.80 g, 4.3 mmol) was heated in POCl3 (10 mL) for 3 hrs. The mixture was concentrated and partitioned in ethyl acetate and water. The organic layer was separated, washed with NaHCO3, dried and concentrated. The residue was crystallized from a mixture of hexane and ethyl acetate to give 2-chloro-5-fluoro-quinoline-3-carbonitrile 32-1 as a white solid (0.83 g). 1HNMR (CDCl3), δ, 8.82 (1H, s), 7.83-7.92 (2H, m), 7.33-7.41 (1H, m).

後処理

  1. concentrationThe mixture was concentrated
  2. custompartitioned in ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with NaHCO3
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was crystallized from a mixture of hexane and ethyl acetate

出典と根拠

ORDレコード
ord-f59e0192801e4e76ad21dee62f941ff3
出典データセット
uspto-grants-2015_02
特許番号
US08952161B2

反応ノート

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