Sodium Hydroxide → {5-Fluoro-2-[(3-Nitrobenzyl)carbamoyl]phenoxy}acetic Acid

HRID 2229542Notes

Reaction equation

HRID 2229542 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14](=[O:26])[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=1)C.[OH-].[Na+]>C(O)C>[F:13][C:11]1[CH:10]=[CH:9][C:8]([C:14](=[O:26])[NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)=[C:7]([CH:12]=1)[O:6][CH2:5][C:4]([OH:27])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22093485[5-Fluoro-2-(3-nitro-benzylcarbamoyl)-phenoxy]-acetic acid ethyl ester

Product 1

HCID 9798381{5-Fluoro-2-[(3-Nitrobenzyl)carbamoyl]phenoxy}acetic AcidYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [5-fluoro-2-(3-nitro-benzylcarbamoyl)-phenoxy]-acetic acid ethyl ester (3.3 g, 8.77 mmol) in ethanol (40 mL) was treated with aq 2 N NaOH (24 mL, 47.8 mmol). After stirring for 4 h, the solution was concentrated in vacuo until most of the ethanol was removed, and the mixture was acidified to pH of 1 with 2 N HCl. After extracting with ethyl acetate, the organic layer was washed with saturated aq NaCl, dried over MgSO; and concentrated to give [5-fluoro-2-(3-nitro-benzylcarbamoyl)-phenoxy]-acetic acid as an off-white solid (3.00 g, 98%): mp 148-151° C.; Rf 0.39 (20% methanol in dichloromethane); 1H NMR (DMSO-d6 300 MHz) δ 9.20 (t, J=6.3 Hz, 1H) 8.18 (s, 1H), 8.09 (dd, J1=7.2 Hz, J2=2.7 Hz, 1 H), 7.90 (dd, J1=8.7 Hz, J2=7.0 Hz, 1H), 7.79 (d, J=7.5 Hz, 1H), 7.61 (t, J=7.8 Hz, 1H), 7.08 (dd, J1=10.8 Hz, J2=2.1 Hz, 1H), 6.91 (dt, J1=8.7 Hz, J2=2.4 Hz, 1H), 4.89 (s, 2H), 4.62 (d, J=6 Hz, 2H). ESI-LC/MS m/z calcd for C16H13FN2O6: 348.3; Found 347.0 (M−1)−. Anal. calcd for C16H13FN2O6: C, 55.18; H, 3.76; N, 8.04. Found C, 55.02; H, 3.79; N, 7.98.

Workup

  1. concentrationthe solution was concentrated in vacuo 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 MgSO
  6. concentrationand concentrated

Sources & evidence

ORD record
ord-8d53dfec0e844d499090e5b13b693437
Source dataset
uspto-grants-2002_07
Patent number
US06420426B1

Reaction notes

Loading…