Benzaldehyde → HCID 58072522、化合物

HRID 2089965ノート

反応式

HRID 2089965 の反応式
[NH2:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[N:3]=1.[CH:19]([CH:21]=O)=O.[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[NH4+:31].[Cl-].OP(O)(O)=O>CO.O>[C:24]1([C:23]2[N:1]([C:2]3[C:7](=[O:8])[CH:6]=[CH:5][N:4]([C:9]4[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:18])[F:17])[CH:10]=4)[N:3]=3)[CH:19]=[CH:21][N:31]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

8

反応物 5

HCID 240BenzaldehydeHCID 1004Phosphoric AcidHCID 7860GlyoxalHCID 25517Ammonium ChlorideHCID 14820794HCID 14820794、化合物

生成物 1

HCID 58072522HCID 58072522、化合物収率 3.1%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A solution of 3-amino-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (200 mg, 0.783 mmol) and glyoxal (40% solution, 0.0895 mL, 0.783 mmol) in MeOH (2 mL) was stirred at room temperature for 20 h. To the solution were added benzaldehyde (0.159 mL, 1.57 mmol) and NH4Cl (84 mg, 1.57 mmol). The mixture was heated to reflux for 90 min. To the mixture was added H3PO4 (0.106 mL). The mixture was heated to reflux for 24 h. The mixture was diluted with water, extracted with AcOEt, washed with NaHCO3 aqueous solution, dried over Na2SO4, filtered, concentrated in vacuo, purified by column chromatography on silica gel (hexane/AcOEt=50/50 to 0/100) and on basic silica gel (hexane/AcOEt=50/50 to 0/100) and recrystallized with AcOEt/heptane to yield the title compound (9.3 mg, 3% yield) as a white solid: mp 204-205° C. 1H NMR (DMSO-d6, 300 MHz): δ ppm 6.82 (1H, d, J=8.0 Hz), 7.20 (1H, d, J=1.6 Hz), 7.33-7.41 (3H, m), 7.44-7.50 (2H, m), 7.62 (1H, s), 7.64-7.81 (4H, m), 9.06 (1H, d, J=8.0 Hz). Anal. Calcd for C20H13F3N4O: C, 62.83; H, 3.43; N, 14.65. Found: C, 62.50; H, 3.64; N, 14.56.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 90 min
  3. temperatureThe mixture was heated
  4. temperatureto reflux for 24 h
  5. extractionextracted with AcOEt
  6. washwashed with NaHCO3 aqueous solution
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. custompurified by column chromatography on silica gel (hexane/AcOEt=50/50 to 0/100) and on basic silica gel (hexane/AcOEt=50/50 to 0/100)
  11. customrecrystallized with AcOEt/heptane

出典と根拠

ORDレコード
ord-358a07f438f84f95a9d0aced782af370
出典データセット
uspto-grants-2013_05
特許番号
US08435995B2

反応ノート

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