Carbon Dioxide → 2-amino-N-(3-fluoro-4-methoxyphenyl)benzamide

HRID 2241224Notes

Reaction equation

HRID 2241224 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[OH-].[Na+].[F:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[NH2:19].C(=O)=O>O1CCOCC1>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:19][C:18]1[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:16]([F:15])[CH:17]=1)=[O:4]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 8359Isatoic AnhydrideHCID 14798Sodium HydroxideHCID 5811103-Fluoro-4-methoxyaniline

Product 1

HCID 433804092-amino-N-(3-fluoro-4-methoxyphenyl)benzamideYield 39%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred suspension of isatoic anhydride (1.63 g, 10 mmol) in 15 mL dioxane at room temperature under nitrogen was added powdered sodium hydroxide followed by 3-fluoro-4-methoxyaniline (1.41 g, 10 mmol). The mixture was immersed in a room temperature oil bath and slowly heated to reflux. Carbon dioxide gas evolution was evident. After stirring at reflux for 2 hours, the reaction mixture was cooled to room temperature and inorganics were filtered off with dioxane. The filtrate was concentrated to dryness to a brown solid. The crude product was dissolved in a minimum of hot 95% EtOH and crystals formed upon cooling. The crystals were filtered off and rinsed with a minimum of ice cold 95% EtOH to give a tan solid (1.0 g, 39%). 1H-NMR (400 MHz, CDCl3) δ 7.66 (br s, 1H), 7.50 (dd, 1H), 7.44 (dd, 1H), 7.26 (m, 1H), 7.17 (m, 1H), 6.95 (m, 1H), 6.71 (m, 2H), 5.50 (br s, 2H), 3.89 (s, 3H).

Workup

  1. additionwas added
  2. customwas immersed in a room temperature
  3. temperatureslowly heated to reflux
  4. temperatureat reflux for 2 hours
  5. filtrationinorganics were filtered off with dioxane
  6. concentrationThe filtrate was concentrated to dryness to a brown solid
  7. dissolutionThe crude product was dissolved in a minimum of hot 95% EtOH and crystals
  8. customformed
  9. temperatureupon cooling
  10. filtrationThe crystals were filtered off
  11. washrinsed with a minimum of ice cold 95% EtOH

Sources & evidence

ORD record
ord-e907fa9f7f3e4839aa8d18b19673a30e
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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