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

HRID 1091797Notes

Reaction equation

HRID 1091797 reaction equation
[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]

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(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).

Workup

  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

Sources & evidence

ORD record
ord-6d1c81a291674fdd83a8c36320dfa5bd
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

Loading…