Triethylamine → 3-((8-Chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzonitrile

HRID 1091797ノート

反応式

HRID 1091797 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].[CH:32]([C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[C:37]#[N:38])=O.C(N(CC)CC)C.O.[NH2:50][NH2:51]>CN(C=O)C.CCO.O.C(Cl)Cl>[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10]([CH2:32][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[C:37]#[N:38])=[N:51][NH:50][C:8]2=[O:31]

参加物

9

反応物 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 90670m-FormylbenzonitrileHCID 86633041(7-Chloro-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromide

生成物 1

HCID 577917833-((8-Chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzonitrile収率 54.5%

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) (10 g, 23.26 mmol) and 3-formylbenzonitrile (3.20 g, 24.43 mmol) were dissolved DCM (60 mL), to this was added triethylamine (4.22 mL, 30.24 mmol) and the reaction was stirred overnight. The reaction mixture was filtered to afford a white solid. To this was added water (40 mL), EtOH (40 mL) and DMF (4 mL). Hydrazine hydrate (11.65 g, 232.64 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 material as a white solid (3.75 g, 54.5% yield), which was used without further purification; 1H NMR (400.132 MHz, DMSO) δ 4.66 (2H, s), 7.53-7.47 (2H, m), 7.68-7.66 (2H, m), 7.81 (1H, t), 7.97 (1H, d), 8.33 (1H, d), 12.55 (1H, s); m/z (LC-MS, ESI−), RT=2.04 (M−H 294).

後処理

  1. filtrationThe reaction mixture was filtered
  2. customto afford a white 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-6d1c81a291674fdd83a8c36320dfa5bd
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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