Sodium hydride → HCID 70111827, compound

HRID 2054186Notes

Reaction equation

HRID 2054186 reaction equation
[H-].[Na+].[Cl-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)C=CC=CC=1.[C:30]1(=[O:42])[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]([CH:40]=O)=[N:32][NH:31]1>CCCCCC.CS(C)=O>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12](/[CH:11]=[CH:40]\[C:33]2[C:34]3[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:30](=[O:42])[NH:31][N:32]=2)[CH:13]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 157289693,4-Dihydro-4-oxo-1-phthalazinecarboxaldehydeHCID 22325077Triphenyl(3-pyridylmethyl)phosphonium chloride

Product 1

HCID 70111827HCID 70111827, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent3×HCID 8058HexaneSolvent

Procedure

Under N2 atmosphere, 723 mg NaH (60% in oil; 18.1 mmol) is washed twice with hexane, 21 ml DMSO is added, and the mixture heated for 20 min to 70° C. (gas evolution). After cooling to RT, the mixture is diluted with 15 ml DMSO, 6.71 g (17.2 mmol) triphenyl(pyridin-3-yl-methyl)phosphonium chloride (for preparation, see 1a) is added in portions, and the blackish-yellow solution is stirred for 10 min (Wittig reagent). A second flask is prepared with 3.0 g (17.2 mmol) phthalazin-1(2H)-one-4-carbaldehyde in 39 ml DMSO under an inert gas. The above Wittig reagent is added and a little DMSO is then rinsed in. After stirring for 75 min at RT, the mixture is poured onto water/EtOAc, the aqueous phase separated off and extracted again twice with EtOAc. The organic phases are washed with water and brine, combined and extracted twice with 1 N HCl and then discarded. The acidic aqueous phases are immediately adjusted to alkaline pH with sat. Na2CO3 solution and extracted three times with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated by evaporation. This yields the title compound as an E/Z mixture: TLC (EtOAc) Rf=0.18/0.22; HPLC5-40 tR=9.2/9.6; FAB-MS (M+H)+=250.

Workup

  1. additionis added
  2. temperaturethe mixture heated for 20 min to 70° C. (gas evolution)
  3. additionis added in portions
  4. washa little DMSO is then rinsed in
  5. additionthe mixture is poured onto water/EtOAc
  6. customthe aqueous phase separated off
  7. extractionextracted again twice with EtOAc
  8. washThe organic phases are washed with water and brine
  9. extractionextracted twice with 1 N HCl
  10. extractionextracted three times with EtOAc
  11. washThe organic phases are washed with water and brine
  12. dry with materialdried (Na2SO4)
  13. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-3018f3934daf46c48972490eed76ac22
Source dataset
uspto-grants-2008_02
Patent number
US07329660B2

Reaction notes

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