Lithium hydroxide, monohydrate → HCID 59354911, compound

HRID 1099441Notes

Reaction equation

HRID 1099441 reaction equation
[CH3:1][N:2]([CH2:15][C:16]([F:19])([F:18])[F:17])[C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[CH:7][N:6]=1)=[O:4].O.[OH-].[Li+]>O1CCCC1.O>[CH3:1][N:2]([CH2:15][C:16]([F:19])([F:17])[F:18])[C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59354912HCID 59354912, compound

Product 1

HCID 59354911HCID 59354911, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To methyl 6-(methyl(2,2,2-trifluoroethyl)carbamoyl)nicotinate (425 mg, 1.54 mmol) in tetrahydrofuran (17 mL) and water (8.5 mL) was lithium hydroxide monohydrate (193 mg, 4.60 mmol) added and the reaction mixture was stirred at ambient temperature over night. The organic solvent was evaporated, 1M hydrochloric acid added until an acidic pH was reached followed by extraction with ethyl acetate (3×25 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to yield 366 mg (91%) of the title compound as a solid; MS (APPI/APCI) m/z 263[M+H+].

Workup

  1. additionadded
  2. customThe organic solvent was evaporated
  3. addition1M hydrochloric acid added until an acidic pH
  4. extractionwas reached followed by extraction with ethyl acetate (3×25 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-938f311ffc334b61ac203578d22b65e4
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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