Formic Acid → 1-Methyl-1H-benzimidazole-5-carboxylic acid

HRID 626241

Reaktionsgleichung

Reaktionsgleichung von HRID 626241
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][CH3:12])[C:5]([OH:7])=[O:6].[CH:13](O)=O>O>[CH3:12][N:11]1[C:10]2[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=2[N:1]=[CH:13]1

Komponenten

4

Edukt 2

HCID 284Formic AcidHCID 115211443-Amino-4-(methylamino)benzoic acid

Produkt 1

HCID 49130631-Methyl-1H-benzimidazole-5-carboxylic acidAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a stirred solution of 3-amino-4-(methylamino)benzoic acid (9 g, 1.0 eq) in 50 mL water, was added 50 mL formic acid and heated at 85° C. overnight. The mixture was cooled, concentrated in vacuo, and dissolved in water. Then 2N HCl was added to adjust pH to 1-3. The suspension was filtered and washed with water to give the product (9.7 g, 84%). 1H NMR (400 MHz, DMSO-d6) δ 9.48 (s, 1H), 8.37 (s, 1H), 8.12 (d, J=8.8 Hz, 1H), 8.00 (d, J=8.8 Hz, 1H), 4.06 (s, 3H).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. dissolutiondissolved in water
  4. additionThen 2N HCl was added
  5. filtrationThe suspension was filtered
  6. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-506f69e4209d47d4b3dc23f790744a31
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309211B2

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