Methanol → HCID 12092493, compound

HRID 533719Notes

Reaction equation

HRID 533719 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.CO.[Li+].[OH-]>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:19][CH:20]=2)=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 7733132HCID 7733132, compound

Product 1

HCID 12092493HCID 12092493, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(4-fluorophenylcarbamoyl)benzoate (2.98 g, 10.9 mmol) in THF (35 mL) was added MeOH (8 mL) and a solution of LiOH (1.79 g, 43.6 mmol) in H2O (8 mL). The reaction was stirred at room temperature for 2 h. The reaction was quenched upon the addition of 1N HCl (50 mL) and extracted with EtOAc (2×60 mL). The organic extracts were dried over MgSO4, and concentrated under vacuum to afford 4-(4-fluorophenylcarbamoyl)benzoic acid (2.43 g, 86%) as a white solid. 1H-nmr (400 MHz, d6-DMSO) δ 10.49 (s, 1H), 8.11-8.02 (m, 4H), 7.87-7.77 (m, 2H), 7.25-7.16 (m, 2H); MS (ESI) m/z 259.9.

Workup

  1. customThe reaction was quenched upon the addition of 1N HCl (50 mL)
  2. extractionextracted with EtOAc (2×60 mL)
  3. dry with materialThe organic extracts were dried over MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6884d32523cf42da955856eba9fe1a29
Source dataset
uspto-grants-2014_10
Patent number
US08853392B2

Reaction notes

Loading…