Methane → HCID 18989436, compound

HRID 2395592Notes

Reaction equation

HRID 2395592 reaction equation
C(=O)(O)[O-].[Na+].[F:6][C:7]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:10]=[CH:9][C:8]=1/[CH:17]=[CH:18]/[CH2:19][N:20]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH2:31][C:32]([O:34]CC)=[O:33])=[N:21]1.C(O)C.C>O>[F:6][C:7]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:10]=[CH:9][C:8]=1/[CH:17]=[CH:18]/[CH2:19][N:20]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH2:31][C:32]([OH:34])=[O:33])=[N:21]1

Participants

6

Reactant 4

HCID 297MethaneHCID 702EthanolHCID 516892Sodium Bicarbonate2×HCID 60204236HCID 60204236, compound

Product 1

HCID 18989436HCID 18989436, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 183.6 g (2.185 mol) of sodium bicarbonate in 4.2 1 of water is rapidly added to a suspension of 474.4 g (1.092 mol) of ethyl (E) -3-[3-[2-fluoro-3-(trifluoromethyl)phenyl]-2-propenyl]-3,4-dihydro-4-oxo-1-phthalazineacetate in 4.2 1 of ethanol and heating is carried out for 2 h at reflux. A solution of 36.7 g (0.436 mol) of sodium bicarbonate in 800 ml of water is added and heating is carried out for 4 h 30 at reflux. 50 g of Norit are added and heating is carried out for a further 1 h at reflux. The mixture is filtered while hot through Hyflo and the ethanol is evaporated under vacuum. The residual aqueous phase is diluted with water to a volume of 10 l, cooled and acidified to pH=2 with 6N HCl (approximately 300 ml). The precipitate obtained is filtered, washed with water and dried under vacuum at 60° C. and then recrystallized from a hexane/ethyl acetate mixture to give a solid melting at 170°-172° C. Weight obtained: 382 g (Yd. 86%)

Workup

  1. temperatureheating
  2. temperatureat reflux
  3. temperatureheating
  4. waitis carried out for 4 h
  5. temperature30 at reflux
  6. temperatureheating
  7. waitis carried out for a further 1 h
  8. temperatureat reflux
  9. filtrationThe mixture is filtered while hot through Hyflo
  10. customthe ethanol is evaporated under vacuum
  11. additionThe residual aqueous phase is diluted with water to a volume of 10 l
  12. temperaturecooled
  13. customThe precipitate obtained
  14. filtrationis filtered
  15. washwashed with water
  16. customdried under vacuum at 60° C.
  17. customrecrystallized from a hexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-ff0827d9157b4c05b18611d596f096fc
Source dataset
uspto-grants-1996_02
Patent number
US05489592

Reaction notes

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