Hydrazine hydrate (1:1) → HCID 15289593, compound

HRID 37491Notes

Reaction equation

HRID 37491 reaction equation
[NH2:1][C:2]1[C:3]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:4][C:5]([Br:18])=[C:6]([C:13](OCC)=[O:14])[C:7]=1[C:8](OCC)=[O:9].O.[NH2:26][NH2:27]>C(O)C>[NH2:1][C:2]1[C:7]2[C:8](=[O:9])[NH:27][NH:26][C:13](=[O:14])[C:6]=2[C:5]([Br:18])=[N:4][C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 15289697HCID 15289697, compound

Product 1

HCID 15289593HCID 15289593, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a mixture of 1 ml of ethanol and 2 ml of hydrazine monohydrate was dissolved 90 mg of 3-amino-6-bromo-4,5-diethoxycarbonyl-2-phenylpyridine, and the mixture was stirred for 2 hours at room temperature. After the solvent was distilled off, the resulting crystals were collected by filtration with ethanol. Water was added to the crystals, and the mixture was neutralized with 1N hydrochloric acid, the resulting crystals were collected by filtration. The crystals were dissolved in a small volume of methanol. After mixing the methanol solution with silica gel, purification by silica gel column chromatography (eluent:ethyl acetate→ethylacetate/methanol 1:1) was conducted, followed by collection by filtration.

Workup

  1. distillationAfter the solvent was distilled off
  2. filtrationthe resulting crystals were collected by filtration with ethanol
  3. additionWater was added to the crystals
  4. filtrationthe resulting crystals were collected by filtration
  5. dissolutionThe crystals were dissolved in a small volume of methanol
  6. additionAfter mixing the methanol solution
  7. customwith silica gel, purification by silica gel column chromatography (eluent:ethyl acetate→ethylacetate/methanol 1:1)
  8. filtrationfollowed by collection by filtration

Sources & evidence

ORD record
ord-7c94303e5f5d4e478424ca15ba4508ab
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

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