Water → HCID 60204236, compound

HRID 2395591Notes

Reaction equation

HRID 2395591 reaction equation
[H-].[Na+].[O:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:6][NH:5]1.Cl[CH2:21][CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[C:25]=1[F:34].O>CN(C=O)C>[F:34][C:25]1[C:26]([C:30]([F:31])([F:32])[F:33])=[CH:27][CH:28]=[CH:29][C:24]=1/[CH:23]=[CH:22]/[CH2:21][N:5]1[C:4](=[O:3])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 348622Ethyl 2-(4-oxo-3,4-dihydrophthalazin-1-yl)acetateHCID 54421939HCID 54421939, compound

Product 1

HCID 60204236HCID 60204236, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

64.8 g (1.62 mol) of a 60% suspension of sodium hydride in oil are added portionwise under a nitrogen atmosphere to a solution of 341.9 g (1.472 mol) of ethyl 3,4-dihydro-4-oxo-1-phthalazineacetate (prepared according to the process described in Patent EP 2895) in 5 l of anhydrous DMF, the temperature being maintained between 25° and 30° C. The addition lasts approximately one hour. The mixture is then heated for 30 minutes at 60° C. The mixture is cooled to room temperature and a mixture of 421.6 g (1.76 mol) of 1-(3-chloro-1-propenyl) -2-fluoro-3-(trifluoromethyl) benzene (prepared according to Example D1) and 98 ml of anhydrous DMF is added over 30 min. The temperature rises to 38° to 40° C. The mixture is then heated for 3 hours at 60° C. and is then allowed to return to room temperature overnight. The mixture is poured into 7 l of water and extracted with 2 times 4 l of ethyl acetate. Washing is carried out with water, the organic phase is dried over Na2SO4, filtered and evaporated under vacuum and the solid obtained is recrystallized from a hexane/ethyl acetate (4/1 ) mixture. Weight obtained: 474.7 g (Yd.=74%) M.p.=104°-106° C.

Workup

  1. customprepared
  2. temperaturethe temperature being maintained between 25° and 30° C
  3. additionThe addition
  4. temperatureThe mixture is cooled to room temperature
  5. additionis added over 30 min
  6. customrises to 38° to 40° C
  7. temperatureThe mixture is then heated for 3 hours at 60° C.
  8. waitto return to room temperature overnight
  9. extractionextracted with 2 times 4 l of ethyl acetate
  10. washWashing
  11. dry with materialthe organic phase is dried over Na2SO4
  12. filtrationfiltered
  13. customevaporated under vacuum
  14. customthe solid obtained
  15. customis recrystallized from a hexane/ethyl acetate (4/1 ) mixture
  16. customWeight obtained

Sources & evidence

ORD record
ord-68a17cdb12124b9a9efd0ad9cf2dec77
Source dataset
uspto-grants-1996_02
Patent number
US05489592

Reaction notes

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