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

HRID 6357

反応式

HRID 6357 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7918Acetic Anhydride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1881b69a76034b96a687673d2018cfa2
出典データセット
uspto-grants-1993_09
特許番号
US05248681

関連ノート

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