HCID 86747524, compound → HCID 19436759, compound

HRID 2395657Notes

Reaction equation

HRID 2395657 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[C:13]([F:28])=[CH:14][C:15]([N+:25]([O-])=O)=[C:16]([CH:24]=2)[O:17][CH2:18][C:19]([O:21]CC)=O)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8]>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[C:3]([C:12]2[C:13]([F:28])=[CH:14][C:15]3[NH:25][C:19](=[O:21])[CH2:18][O:17][C:16]=3[CH:24]=2)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:8])[F:9]

Participants

4

Reactant 1

HCID 86747524HCID 86747524, compound

Product 1

HCID 19436759HCID 19436759, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2.3 g (5.4 mmole) (5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluoro-2-nitrophenoxy)acetic acid, ethyl ester in 50 mL acetic acid was heated to 80° C. under a nitrogen atmosphere. The heat and nitrogen were removed and 0.9 g (16.2 mmole) iron powder was added in 3 portions over 5 minutes. The solution was stirred at 80° C. for an additional 50 minutes. The solution was cooled and filtered through Celite®. The filtrate was diluted with 100 mL water and extracted three times with ethyl acetate. The ethyl acetate extracts were washed with a saturated NaHCO3 solution, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was recrystallized from methylcyclohexane/ethyl acetate to give 0.96 g (50%) of 7-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-6-fluoro-2H-1,4-benzoxazin-3(4H)-one as a white solid, mp 242° C.

Workup

  1. temperatureThe heat
  2. customnitrogen were removed
  3. temperatureThe solution was cooled
  4. filtrationfiltered through Celite®
  5. additionThe filtrate was diluted with 100 mL water
  6. extractionextracted three times with ethyl acetate
  7. washThe ethyl acetate extracts were washed with a saturated NaHCO3 solution
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was recrystallized from methylcyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-b61715d7fac846d0b7c9b928298dcb79
Source dataset
uspto-grants-1996_02
Patent number
US05489571

Reaction notes

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