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

HRID 854081

Reaction equation

HRID 854081 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
180 °C

Procedure

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−);

Workup

  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

Sources & evidence

ORD record
ord-3e51b983288c4ce384e6fa03fc843185
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Linked notes

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