4-Nitrobenzoic Acid → 2-(4-Nitro-phenyl)-3H-imidazo[4,5-c]pyridine-6-ylamine

HRID 854081

Reaktionsgleichung

Reaktionsgleichung von HRID 854081
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[CH:4][N:3]=1.[N+:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=O)=[CH:15][CH:14]=1)([O-:12])=[O:11].C([O-])([O-])=O.[K+].[K+]>>[N+:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17]2[NH:9][C:5]3[CH:4]=[N:3][C:2]([NH2:1])=[CH:7][C:6]=3[N:8]=2)=[CH:15][CH:14]=1)([O-:12])=[O:11]

Komponenten

4

Edukt 3

HCID 61084-Nitrobenzoic AcidHCID 11430Potassium CarbonateHCID 21813897Pyridine-2,4,5-triamine

Produkt 1

HCID 589329182-(4-Nitro-phenyl)-3H-imidazo[4,5-c]pyridine-6-ylamineAusbeute 56 %

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

2,4,5 Triaminopyridine (6, 0.660 g, 5.32 mmol), p-nitro benzoic acid (7, 0.888 mg 5.32 mmol) was taken in PPA (30 g) and heated at 180° C. for 7 h. The reaction mixture was cooled to room temperature and poured on to crushed ice. The excess PPA was neutralized carefully by addition of solid K2CO3 portion wise (caution) till effervescence ceased. The brownish green precipitate was filtered and washed with water and dried. The solid was taken in (CH2Cl2: MeOH:THF:NH4OH 50:30:17:3) mixture and filtered (repeated the process 3-4 times). The solvents were removed and the nitro amine precipitated with EtOAc to give 8 (0.575 g, 56%). 1H NMR (DMSO-d6; 500 MHz): δ11.10 (1H, brs), 8.77 (1H, s), 8.45-8.25 (4H m), 6.50 (1H, s), 5.67 (2H, brs); EIMS m/z: 256.4 (M+1) and 290 (M+Cl−);

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionpoured on
  3. customto crushed ice
  4. filtrationThe brownish green precipitate was filtered
  5. washwashed with water
  6. customdried
  7. filtrationfiltered (
  8. customThe solvents were removed
  9. customthe nitro amine precipitated with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-3e51b983288c4ce384e6fa03fc843185
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07256287B2

Verknüpfte Notizen

Wird geladen…