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

HRID 1091782노트

반응식

HRID 1091782 반응식
[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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 702Ethanol용매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-b7007d6824c54f59b0065e0185702814
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129380B2

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