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

HRID 457954Notes

Reaction equation

HRID 457954 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 MgSO4 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, 1 H) 8.18 (s, 1 H), 8.09 (dd, J1=7.2 Hz, J2=2.7 Hz, 1 H), 7.90 (dd, J1=8.7 Hz, J2=7.0 Hz, 1 H), 7.79 (d, J=7.5 Hz, 1 H), 7.61 (t, J=7.8 Hz, 1 H), 7.08 (dd, J1=10.8 Hz, J2=2.1 Hz, 1 H), 6.91 (dt, J1=8.7 Hz, J2=2.4 Hz, 1 H), 4.89 (s, 2 H), 4.62 (d, J=6 Hz, 2 H). 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 MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-57ca775d10d84d779b76a384bee12439
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Reaction notes

Loading…