Aniline → HCID 178420476, compound

HRID 868494Notes

Reaction equation

HRID 868494 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[N:10][C:3]=12.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1C=CC=CC=1>[NH:11]([C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[N:10][C:3]=12)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 178478247HCID 178478247, compound

Product 1

HCID 178420476HCID 178420476, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
130 °C

Procedure

To 7-chloro-3H-imidazo(4,5-b)pyridine (16 g, 97 mmol) was added aniline (200 mL, 2.1 mol). The resulting mixture was heated under a nitrogen atmosphere at 130° C. for 24 hours. Benzene was added to the cooled mixture and the precipitate was filtered. The solid was dissolved in water and 1N NaOH was added to give a pH reading of 9. The precipitate was filtered and recrystallized from EtOH (decolorized by charcoal) to give 7.2 g (35%) of the 7-anilino-3H-imidazo[4,5-b]pyridine, m.p. 251°-252° C.

Workup

  1. filtrationthe precipitate was filtered
  2. dissolutionThe solid was dissolved in water
  3. addition1N NaOH was added
  4. customto give a pH reading of 9
  5. filtrationThe precipitate was filtered
  6. customrecrystallized from EtOH (decolorized by charcoal)

Sources & evidence

ORD record
ord-59b59e1f99e742fbb2f87a42ca359448
Source dataset
uspto-grants-1988_10
Patent number
US04780452

Reaction notes

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