Triethyl orthoacetate → 4-(2-Methyl-1H-imidazo[4,5-c]pyridin-1-yl)benzonitrile

HRID 249254Notes

Reaction equation

HRID 249254 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.[C:17](OCC)(OCC)(OCC)[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 66221Triethyl orthoacetateHCID 105364203-Amino-4-[N-(4-cyanophenyl)amino]pyridine

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-[N-(4-cyanophenyl)amino]pyridine (see part (b)) (9.31 g, 44.3 mmol), triethyl orthoacetate (40 ml) and acetic anhydride (30 ml) was heated under 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 the title compound (6.5 g), as a brown solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours under nitrogen
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure The brown residue
  5. dissolutionwas 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-1cc3e249fc994216b926e4fcdae258b3
Source dataset
uspto-grants-1993_05
Patent number
US05214044

Reaction notes

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