Methane → 2-[(4-Methoxyphenyl)amino]benzoic acid

HRID 1662934

Reaktionsgleichung

Reaktionsgleichung von HRID 1662934
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.Cl[C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].C(=O)([O-])[O-].[Na+].[Na+].C>O.C(O)CO>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:11]2[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 297MethaneHCID 7732P-AnisidineHCID 83742-Chlorobenzoic AcidHCID 10340Sodium Carbonate

Produkt 1

HCID 2029182-[(4-Methoxyphenyl)amino]benzoic acidAusbeute 49,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 174Ethylene GlycolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

4-Methoxyaniline (1.86 gm; 20 mmol), 2-chlorobenzoic acid (1.56 gm; 10 mmol), ethylene glycol (5 ml) and anhydrous sodium carbonate (1.1 gm; 10 mmol) were placed in a reaction vessel and stirred until effervescence ceased. Cupric chloride (100 mg; 0.75 mmol) dissolved in 2 ml of water was added to the reaction mixture which was then heated to 125° C. for 6 hours. The reaction was allowed to cool then water (30 ml) and charcoal were added. The mixture was filtered and acidified to pH 2 with conc. hydrochloric acid. The precipitate was collected by filtration, washed with water and then re-dissolved in 1M sodium hydroxide solution. Material was re-precipitated by the addition of acetic acid, filtered off, washed with aqueous acetic acid, then water and finally dried under vacuum over phosphorous pentoxide to give 1200 mg (49%) of N-(4-methoxyphenyl)anthranilic acid.

Aufarbeitung

  1. additionwas added to the reaction mixture which
  2. temperatureto cool
  3. filtrationThe mixture was filtered
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. dissolutionre-dissolved in 1M sodium hydroxide solution
  7. customMaterial was re-precipitated by the addition of acetic acid
  8. filtrationfiltered off
  9. washwashed with aqueous acetic acid
  10. dry with materialwater and finally dried under vacuum over phosphorous pentoxide

Quellen und Nachweise

ORD-Eintrag
ord-abef91a7a1624203b5bda919b96a9a39
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08034558B2

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