Hydrazine hydrate (1:1) → 2-(2-Methoxy-4-amino-5-nitro-phenyl)-5-methoxy-imidazo[4,5-b]pyridine

HRID 3872Notes

Reaction equation

HRID 3872 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2C(=O)C(C)(C)C3C(=CC([N+]([O-])=O)=CC=3)C2=O)[C:6]([N+:26]([O-:28])=[O:27])=[CH:5][C:4]=1[C:29]1[NH:30][C:31]2[C:32]([N:39]=1)=[N:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=2.O.NN>C(O)(C)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[C:6]([N+:26]([O-:28])=[O:27])=[CH:5][C:4]=1[C:29]1[NH:30][C:31]2[C:32]([N:39]=1)=[N:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 201532782-[2-methoxy-5-nitro-4-(4,4-dimethyl-7-nitro-2H,4H-isoquinolin-1,3-dione-2-yl)-phenyl]-5-methoxy-imidazo[4,5-b]pyridine

Product 1

HCID 201532722-(2-Methoxy-4-amino-5-nitro-phenyl)-5-methoxy-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

One half gram of 2-[2-methoxy-5-nitro-4-(4,4-dimethyl-7-nitro-2H,4H-isoquinolin-1,3-dione-2-yl)-phenyl]-5-methoxy-imidazo[4,5-b]pyridine is suspended in 10 ml of isopropanol, mixed with 0.5 ml of 80% hydrazine hydrate, and refluxed for 1.75 hours with stirring. The reaction mixture is concentrated by evaporation, the residue is triturated with 50 ml of ice water, and the product precipitated is purified by chromatography on silica gel [eluant: methylene chloride/ethanol (100:0 to 100:2)].

Workup

  1. temperaturerefluxed for 1.75 hours
  2. concentrationThe reaction mixture is concentrated by evaporation
  3. customthe residue is triturated with 50 ml of ice water
  4. customthe product precipitated
  5. customis purified by chromatography on silica gel [eluant: methylene chloride/ethanol (100:0 to 100:2)]

Sources & evidence

ORD record
ord-f3d5d152d9a34241b654d7e6361c94bd
Source dataset
uspto-grants-1988_02
Patent number
US04722929

Reaction notes

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