Hydrazine → 4-Bromopyridazine-3,6-diol

HRID 380324

反応式

HRID 380324 の反応式
O.[NH2:2][NH2:3].[Br:4][C:5]1[C:6](O[C:9](=[O:11])[CH:10]=1)=[O:7].NN>C1COCC1>[Br:4][C:5]1[C:6](=[O:7])[NH:2][NH:3][C:9](=[O:11])[CH:10]=1

参加物

5

反応物 3

HCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 800273-Bromo-2,5-furandione

生成物 1

HCID 2549424-Bromopyridazine-3,6-diol収率 77%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Hydrazine hydrate (28 ml, 576 mmol) was added dropwise to a stirred solution of bromomaleic anhydride (100 g, 565 mmol) in THF (1 l) cooled in an ice-bath so that the internal temperature did not exceed 10° C. After complete addition of the hydrazine the mixture was refluxed for 18 h. Solvent was removed by evaporation and the residues were dried by azeotroping with toluene. The residue was triturated and washed with diethyl ether to give the title compound as an orange solid (83 g, 77%). 1H NMR (250 MHz , d6-DMSO) δ 7.68 (1H, br s). MS (ES+) m/e 193 [MH]+, 191 [MH]+. This material was used without further purification.

後処理

  1. temperaturecooled in an ice-bath so that the internal temperature
  2. customdid not exceed 10° C
  3. temperaturewas refluxed for 18 h
  4. customSolvent was removed by evaporation
  5. customthe residues were dried
  6. customby azeotroping with toluene
  7. customThe residue was triturated
  8. washwashed with diethyl ether

出典と根拠

ORDレコード
ord-d910e63b15bf4e63a4ea8b86dbac71fa
出典データセット
uspto-grants-2001_10
特許番号
US06303605B1

関連ノート

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