HCID 86639325, compound → HCID 67102240, compound

HRID 2079685Notes

Reaction equation

HRID 2079685 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[C:6]([O:14][CH3:15])[C:5]=1[NH:16]C(=O)CC(=O)C>[OH-].[Na+]>[NH2:16][C:5]1[C:6]([O:14][CH3:15])=[CH:7][CH:8]=[C:9]([C:10]([F:11])([F:12])[F:13])[C:4]=1[C:3]([OH:23])=[O:2]

Participants

3

Reactant 1

HCID 86639325HCID 86639325, compound

Product 1

HCID 67102240HCID 67102240, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl-2-(acetylacetamido)-3-methoxy-6-(trifluoromethyl)benzoate in 2N NaOH was heated to reflux for 4-5 h. The reaction mixture was cooled and pH was adjusted to 2. The product was extracted in ethyl acetate. The ethyl acetate extracts were combined, washed with brine and dried over sodium sulfate. Filtered, evaporated and residue was triturated with hexane. The solid was collected by filtration and dried under vacuum to provide product as light brown solid in 85% yield. ES/MS m/z 236.0 (MH+).

Workup

  1. temperatureto reflux for 4-5 h
  2. temperatureThe reaction mixture was cooled
  3. extractionThe product was extracted in ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltered
  7. customevaporated
  8. customresidue was triturated with hexane
  9. filtrationThe solid was collected by filtration
  10. customdried under vacuum
  11. customto provide product as light brown solid in 85% yield

Sources & evidence

ORD record
ord-3ce2e07e18574f9697fdb7c0d5bc052d
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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