Hydrochloric Acid → 5-Iodo-2-(methylamino)benzoic acid

HRID 865351

Reaktionsgleichung

Reaktionsgleichung von HRID 865351
[CH3:1][NH:2][C:3]1[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:5]([OH:7])=[O:6].Cl.[I:13]Cl>O>[I:13][C:9]1[CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]([NH:2][CH3:1])=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric Acid2×HCID 24640Iodine chlorideHCID 67069N-Methylanthranilic acid

Produkt 1

HCID 222818675-Iodo-2-(methylamino)benzoic acidAusbeute 94.626,898 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

In a 1 L beaker was placed 40 grams (0.267 mmol) of N-methylanthranilic acid dissolved in 300 mL water and 26.7 mL conc. HCl cooled to 20° C. A solution of ICL, prepared by dissolving 44 grams of ICl to a cooled (0° C.) solution of 167 mL water and 45 ml conc. HCl, was rapidly added to the stirred N-methylanthranilc acid solution. The reaction was allowed to stir for 2 hrs, filtered on a medium glass frit funnel, washing the solids with water. The green powder isolated was dried under vacuum to yield 70 grams (96%) of 5-iodo-N-methylanthranilic acid. 1H NMR (DMSO-d6) 7.61 (1H, bs, C6-H), 7.21 (1H, bd, 3JHH =8 Hz, C4-H), 6.19 (1H, d, 3JHH =8 Hz, C3-H), 2.43 (3H, s, NCH3); 13C NMR (DMSO-d6) 169.0, 151.4, 142.7, 139.6, 114.2, 112.7, 74.2, 29.6.

Aufarbeitung

  1. customA solution of ICL, prepared
  2. additionwas rapidly added to the stirred N-methylanthranilc acid solution
  3. filtrationfiltered on a medium glass frit funnel
  4. washwashing the solids with water
  5. customThe green powder isolated
  6. customwas dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f497eefb671b463b9bb8cbd8dc4c197a
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05565449

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