3-[(2-Dimethylamino-4-nitro-benzoyl)-amino]-2-amino-6-methoxy-pyridine → 2-(2-Dimethylamino-4-nitro-phenyl)-5-methoxy-imidazo[4,5-b]pyridine

HRID 3852Notes

Reaction equation

HRID 3852 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:4]=1[C:5]([NH:7][C:8]1[C:9]([NH2:16])=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)=O>P(Cl)(Cl)(Cl)=O>[CH3:1][N:2]([CH3:24])[C:3]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:4]=1[C:5]1[NH:7][C:8]2[C:9]([N:16]=1)=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=2

Participants

3

Reactant 1

HCID 135324023-[(2-Dimethylamino-4-nitro-benzoyl)-amino]-2-amino-6-methoxy-pyridine

Product 1

HCID 135323492-(2-Dimethylamino-4-nitro-phenyl)-5-methoxy-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A suspension of 1.4 gm of 3-[(2-dimethylamino-4-nitro-benzoyl)-amino]-2-amino-6-methoxy-pyridine in 40 ml of phosphorus oxychloride is refluxed for three hours. The phosphorus oxychloride is evaporated off by about two-thirds, and the residue is poured into water. The solution obtained is made ammoniacal, and the product precipitated is purified over a silica gel column [eluant: methylene chloride/ethanol (100:0 to 100:0.5)].

Workup

  1. temperatureis refluxed for three hours
  2. customThe phosphorus oxychloride is evaporated off by about two-thirds
  3. additionthe residue is poured into water
  4. customThe solution obtained
  5. customthe product precipitated
  6. customis purified over a silica gel column [eluant: methylene chloride/ethanol (100:0 to 100:0.5)]

Sources & evidence

ORD record
ord-072da412b7c74d68ae2b0cbe80cf9367
Source dataset
uspto-grants-1988_02
Patent number
US04722929

Reaction notes

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