3-Amino-4-[N-(4-cyanophenyl)amino]pyridine → 4-(2-Methyl-1H-imidazo[4,5-c]pyridin-1-yl)benzonitrile

HRID 892761Notes

Reaction equation

HRID 892761 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1.[CH2:17](C(CC)(CC)C([O-])([O-])[O-])[CH3:18]>C(OC(=O)C)(=O)C>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([N:8]2[C:7]3[CH:6]=[CH:5][N:4]=[CH:3][C:2]=3[N:1]=[C:17]2[CH3:18])=[CH:10][CH:11]=1)#[N:16]

Participants

4

Reactant 2

HCID 105364203-Amino-4-[N-(4-cyanophenyl)amino]pyridineHCID 21875354Triethylorthoaceate

Product 1

HCID 106811874-(2-Methyl-1H-imidazo[4,5-c]pyridin-1-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 3-amino-4-(4'-cyanophenyl)aminopyridine (9.31 g, 44.3 mmol), triethyl-orthoacetate (40 ml) and acetic anhydride (30 ml) was heated at reflux for 2 hours under nitrogen, cooled, then concentrated under reduced pressure. The brown residue was dissolved in 1M hydrochloric acid and washed with ethyl acetate (200 ml). The aqueous layer was rendered basic with saturated aqueous ammonia and extracted with dichloromethane (3×200 ml). The combined extracts were washed with water, dried (MgSO4) and concentrated to give 1-(4-cyanophenyl)-2-methylimidazo[4,5-c]pyridine, 6.5 g, as a brown solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours under nitrogen
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe brown residue was dissolved in 1M hydrochloric acid
  6. washwashed with ethyl acetate (200 ml)
  7. extractionextracted with dichloromethane (3×200 ml)
  8. washThe combined extracts were washed with water
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f00ccfa8217b46db8265b5368d3a328e
Source dataset
uspto-grants-1992_06
Patent number
US05120747

Reaction notes

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