Phosphorus oxychloride → 1-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline

HRID 375845ノート

反応式

HRID 375845 の反応式
[CH2:1]([N:3]1[C:7]([NH:8][C:9]2[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11](O)=O)=[CH:6][CH:5]=[N:4]1)[CH3:2].P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:11]1[C:10]2[C:9](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]=[C:7]2[N:3]([CH2:1][CH3:2])[N:4]=[CH:5][C:6]=12

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 154274682-((1-Ethyl-1H-pyrazol-5-yl)amino)benzoic acid

生成物 1

HCID 158169081-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline収率 81.7%

実験手順

A mixture of N-(1-ethylpyrazol-5-yl)anthranilic acid (21.4 g, 0.0925 mol) and phosphorous oxychloride (312.8 g, 2.04 mol) was refluxed for 3 hours and then was stirred at room temperature overnight. The POCl3 was removed by distillation, and the residue was poured into ice-water. The solution was neutralized with 35% NaOH and extracted with CH2Cl2 (4×). The organic layer was separated, washed with water, then brine and then was dried over MgSO4. The solvent was concentrated in vacuo and the residue was purified by column chromatography on silica gel eluting with CH2Cl2 to afford 17.5 g (81.7%) of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]quinoline. Alternatively, the reaction was run as described above and then was worked up by neutralization with concentrated NH4OH to a pH of 8 and then the product, which crystallized directly from the solution, was collected by filtration.

後処理

  1. temperaturewas refluxed for 3 hours
  2. customThe POCl3 was removed by distillation
  3. additionthe residue was poured into ice-water
  4. extractionextracted with CH2Cl2 (4×)
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialbrine and then was dried over MgSO4
  8. concentrationThe solvent was concentrated in vacuo
  9. customthe residue was purified by column chromatography on silica gel eluting with CH2Cl2

出典と根拠

ORDレコード
ord-defb337e1a5f406b93746b470be0a916
出典データセット
uspto-grants-1996_01
特許番号
US05488055

反応ノート

読み込み中…