Benzaldehyde → 1H-Imidazo(4,5-c)pyridine, 4-chloro-2-phenyl-

HRID 1863944Notes

Reaction equation

HRID 1863944 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([NH2:9])[CH:5]=[CH:4][N:3]=1.[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[N+](C1C=CC=CC=1)([O-])=O.O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>>[Cl:1][C:2]1[C:7]2[N:8]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:9][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 7416NitrobenzeneHCID 2857362-Chloropyridine-3,4-diamineHCID 71586775Bentonite

Product 1

HCID 54883681H-Imidazo(4,5-c)pyridine, 4-chloro-2-phenyl-

Conditions

Temperature
175 °C

Procedure

A mixture of 100 mg (0.696 mmol) of 2-chloropyridine-3,4-diamine [H. Dvorakova et al., Collect. Czech. Chem. Commun., 58, 629 (1993)], 0.086 mL (0.835 mmol) of benzaldehyde, and 2 mL of nitrobenzene was heated at 175° C. under microwave irradiation for 30 min. The cooled solution was treated with 500 mg of Montmorillonite K 10 clay, and microwave irradiation at 175° C. was continued for an additional 30 min. The cooled mixture was filtered through Celite, and the filter cake was washed with methanol. The combined filtrate and washings were concentrated to dryness. Flash chromatography of the residue on silica gel (0-5% methanol in dichloromethane) yielded the title compound as a foam. LC-MS 230 (M+1).

Workup

  1. filtrationThe cooled mixture was filtered through Celite
  2. washthe filter cake was washed with methanol
  3. concentrationThe combined filtrate and washings were concentrated to dryness

Sources & evidence

ORD record
ord-0d46e9c67dc74a95afb75bb1116e2ebc
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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