Acetic Acid → Phenyl(pyridazin-4-yl)methanone

HRID 512193

反応式

HRID 512193 の反応式
[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(O)=[O:16]>>[C:2]1([C:1]([C:8]2[CH:13]=[CH:12][N:11]=[N:10][CH:9]=2)=[O:16])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

3

反応物 2

HCID 176Acetic Acid2 回HCID 5984154-Benzylpyridazine

生成物 1

HCID 12486783Phenyl(pyridazin-4-yl)methanone収率 91%

反応条件

温度
100 °C

実験手順

A solution of 4-benzylpyridazine (1.0 g, 5.9 mmol) in AcOH (28 mL) was added dropwise to a stirring suspension of SeO2 (3.2 g, 29.5 mmol) in AcOH (28 mL), the resulting mixture was heated to 100° C. for 1 h. TLC showed the starting material had disappeared, then the reaction solution was filtrated, the filtration was concentrated under reduced pressure, and Sat.aq Na2CO3 was added to adjust PH=9-10, then, extracted with DCM (50 mL×3), washed by brine, dried over Na2SO4 and concentrated to get the phenyl(pyridazin-4-yl)methanone (1.0 g, yield: 91%). 1H NMR (CDCl3 400 MHz): δ9.50-9.45 (m, 2H), 7.83 (d, J=7.6 Hz, 2H), 7.78-7.74 (dd, J=5.2, 2.4 Hz, 1H), 7.74-7.68 (m, 1H), 7.57 (t, J=7.2 Hz, 2H).

後処理

  1. filtrationthe reaction solution was filtrated
  2. filtrationthe filtration
  3. concentrationwas concentrated under reduced pressure, and Sat.aq Na2CO3
  4. additionwas added
  5. extractionextracted with DCM (50 mL×3)
  6. washwashed by brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-9ff593f467354e5ba3227a793ad1ce01
出典データセット
uspto-grants-2015_08
特許番号
US09102591B2

関連ノート

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