6-Methoxy-2,3-pyridinediamine HCl → 2-(2-Dimethylamino-4-nitro-phenyl)-5-methoxy-imidazo[4,5-b]pyridine

HRID 3853Notes

Reaction equation

HRID 3853 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:4]=1[C:5](O)=O.Cl.Cl.[NH2:18][C:19]1[C:24]([NH2:25])=[CH:23][CH:22]=[C:21]([O:26][CH3:27])[N:20]=1>P(Cl)(Cl)(Cl)=O>[CH3:1][N:2]([CH3:15])[C:3]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:4]=1[C:5]1[NH:25][C:24]2[C:19]([N:18]=1)=[N:20][C:21]([O:26][CH3:27])=[CH:22][CH:23]=2

Participants

4

Reactant 2

HCID 30239196-Methoxy-2,3-pyridinediamine HClHCID 201382202-(Dimethylamino)-4-nitrobenzoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

An amount of 0.45 gm of 2-dimethylamino-4-nitro-benzoic acid is suspended in 15 ml of phosphorus oxychloride, and 0.45 gm of 2,3-diamino-6-methoxy-pyridine dihydrochloride are added. The mixture is refluxed for two hours and after cooling poured onto water. The aqueous solution is made ammoniacal with cooling, and the product precipitated is treated as in Example 4(b).

Workup

  1. temperatureThe mixture is refluxed for two hours
  2. temperatureafter cooling
  3. additionpoured onto water
  4. temperaturewith cooling
  5. customthe product precipitated
  6. additionis treated as in Example 4(b)

Sources & evidence

ORD record
ord-2a7e3c04034f4962805f2b8605f567fe
Source dataset
uspto-grants-1988_02
Patent number
US04722929

Reaction notes

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