Sodium Hydroxide → 4-Fluoro-2-methoxy-5-morpholin-4-yl-benzoic acid

HRID 2229574Notes

Reaction equation

HRID 2229574 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[C:7]([F:16])=[CH:6][C:5]=1[O:17][CH3:18].[OH-].[Na+]>C(O)C>[F:16][C:7]1[C:8]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)=[CH:9][C:4]([C:3]([OH:19])=[O:2])=[C:5]([O:17][CH3:18])[CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 220934904-Fluoro-2-methoxy-5-morpholin-4-yl-benzoic acid methyl ester

Product 1

HCID 184682204-Fluoro-2-methoxy-5-morpholin-4-yl-benzoic acidYield 79.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 4-fluoro-2-methoxy-5-morpholin-4-yl-benzoic acid methyl ester (1.2.0 g, 4.46 mmol) in ethanol (22.0 mL) was treated with aq 2 N NaOH (13 mL, 26.7 mmol). The mixture was stirred at room temperature for 2 h, concentrated until most of the ethanol was removed and acidified with aq 2 N HCl to pH 1. After extracting with ethyl acetate, the organic layer was washed with saturated aq NaCl, dried over MgSO4 and concentrated to give 4-fluoro-2-methoxy-5-morpholin-4-yl-benzoic acid (0.90 g, 79%): 1H NMR (DMSO-d6 300 MHz) δ 12.62 (s, 1H), 7.34 (d, J=10.5 Hz, 1H), 7.04 (d, J=14.7 Hz, 1H), 3.76 (s, 3H), 3.70 (t, J=4.7 Hz, 4H), 2.90 (t, J=4.7 Hz, 4H).

Workup

  1. concentrationconcentrated until most of the ethanol
  2. customwas removed
  3. extractionAfter extracting with ethyl acetate
  4. washthe organic layer was washed with saturated aq NaCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-886aade9ff41464283d3cc3d7f9f78dc
Source dataset
uspto-grants-2002_07
Patent number
US06420426B1

Reaction notes

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