Triethylamine → 5-((8-Chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)-2-fluorobenzonitrile

HRID 1091782ノート

反応式

HRID 1091782 の反応式
[Br-].[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[CH:10]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)O[C:8]2=[O:31].[F:32][C:33]1[CH:40]=[CH:39][C:38]([CH:41]=O)=[CH:37][C:34]=1[C:35]#[N:36].C(N(CC)CC)C.O.[NH2:51][NH2:52]>C(Cl)Cl.CN(C=O)C.CCO.O>[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10]([CH2:41][C:38]1[CH:39]=[CH:40][C:33]([F:32])=[C:34]([CH:37]=1)[C:35]#[N:36])=[N:52][NH:51][C:8]2=[O:31]

参加物

9

反応物 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 27695822-Fluoro-5-formylbenzonitrileHCID 86633041(7-Chloro-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromide

生成物 1

HCID 577918005-((8-Chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)-2-fluorobenzonitrile収率 90%

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

(7-chloro-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromide (101) (9.3 g, 21.64 mmol) and 2-fluoro-5-formylbenzonitrile (3.55 g, 23.80 mmol) were dissolved in DCM (60 mL), to this was added triethylamine (3.92 mL, 28.13 mmol) and the reaction was stirred overnight. The reaction mixture was evaporated to afford a brown solid. To this was added water (40 mL), EtOH (40 mL) and DMF (4 mL). Hydrazine hydrate (10.83 g, 216.35 mmol) was added and the reaction was heated at reflux overnight. The reaction was cooled and the precipitate was collected by filtration, washed with EtOH (25 mL) and air dried to afford the desired compound as a yellow solid (6.10 g, 90%), which was used without further purification; 1H NMR (400.132 MHz, DMSO) δ 4.64 (2H, s), 7.44 (1H, t), 7.63-7.59 (1H, m), 7.78 (1H, dd), 7.81 (1H, t), 7.98 (1H, dd), 8.33 (1H, dd); m/z (LC-MS, ESI+), RT=2.17 (M−H 312).

後処理

  1. customThe reaction mixture was evaporated
  2. customto afford a brown solid
  3. temperaturethe reaction was heated
  4. temperatureat reflux overnight
  5. temperatureThe reaction was cooled
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with EtOH (25 mL) and air
  8. customdried

出典と根拠

ORDレコード
ord-b7007d6824c54f59b0065e0185702814
出典データセット
uspto-grants-2012_03
特許番号
US08129380B2

反応ノート

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