Phosphorus oxychloride → 4-Chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid

HRID 15970ノート

反応式

HRID 15970 の反応式
O[C:2]1[C:3]([C:11]([OH:13])=[O:12])=[N:4][N:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8].O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:2]1[C:3]([C:11]([OH:13])=[O:12])=[N:4][N:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8]

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 574421684-Hydroxy-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid

生成物 1

HCID 666732574-Chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid収率 60%

反応条件

温度
85 °C

実験手順

A mixture of 4-hydroxy-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid (876 mg, 4.76 mmol) and POCl3 (4.5 mL) was heated for 24 hours at 85° C. POCl3 was removed under reduced pressure. The crude material was quenched with ice. The reaction mixture was stirred for 1 hour at room temperature. After removing solids by filtration, the aqueous filtrate was extracted with EtOAc (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to give. The recovered material was combined with the solids previously isolated and triturated with ether to afford 577 mg (60%) of the desired product.

後処理

  1. customPOCl3 was removed under reduced pressure
  2. customThe crude material was quenched with ice
  3. customAfter removing solids
  4. filtrationby filtration
  5. extractionthe aqueous filtrate was extracted with EtOAc (3×)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give
  10. custompreviously isolated
  11. customtriturated with ether

出典と根拠

ORDレコード
ord-c71b32b0448d43e49c84e64943d86824
出典データセット
uspto-grants-2010_06
特許番号
US07732616B2

反応ノート

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