Hydrochloric Acid → HCID 22268744, compound

HRID 270232Notes

Reaction equation

HRID 270232 reaction equation
FC(F)(F)[C:3]([NH:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1)[C:9]([O:11]C)=[O:10])=O.C[Si]([N-][Si](C)(C)C)(C)C.[K+].IC.[OH-].[Li+].Cl>C1COCC1>[CH3:3][NH:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:15]=1)[C:9]([OH:11])=[O:10]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6328Methyl iodideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 22268778HCID 22268778, compound

Product 1

HCID 22268744HCID 22268744, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(trifluoromethylcarbonyl)amino-5-(trifluoromethyl)benzoate (cf. procedures (116a) and (80a); 131 mg, 0.42 mmol) was dissolved in THF (5 mL), and the resultant solution was charged successively with KHMDS (0.83 mL of a 0.5 M solution) and iodomethane (0.03 mL, 0.42 mL). The mixture was stirred for 16 h, quenched with sat. NaHCO3, and extracted with EtOAc (2×). The organic extracts were combined, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. This product was dissolved in 3:1:1 THF/MeOH/water (5 mL) and the resultant solution was charged with lithium hydroxide (20 mg, 0.84 mmol). The reaction was stirred for 14 h, acidified with 1N HCl, and extracted with EtOAc (2×). The organic extracts were combined, washed with water, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide 3-methylamino-5-(trifluoromethyl)benzoic acid.

Workup

  1. customquenched with sat. NaHCO3
  2. extractionextracted with EtOAc (2×)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThis product was dissolved in 3:1:1 THF/MeOH/water (5 mL)
  8. stirringThe reaction was stirred for 14 h
  9. extractionextracted with EtOAc (2×)
  10. washwashed with water
  11. washwashed with brine
  12. dry with materialdried (Na2SO4)
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e3d6045ff83b49f59b67f7e38c61524c
Source dataset
uspto-grants-2008_11
Patent number
US07449493B2

Reaction notes

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