Methane → HCID 21882728, compound

HRID 722060Notes

Reaction equation

HRID 722060 reaction equation
C.[NH2:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][C:6]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)=[CH:5][N:4]=1.O.NN>CO>[NH2:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([C:12]2[CH:13]=[CH:14][C:15]([Br:18])=[CH:16][CH:17]=2)=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 24654Hydrazine hydrate (1:1)HCID 21882699HCID 21882699, compound

Product 1

HCID 21882728HCID 21882728, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.145 g of ferric chloride and 0.12 g of activated charcoal are added to a suspension of 0.98 g of 2-amino-5-(4-bromphenyl)-3-nitropyridine (starting material H2) in 30 ml of methanol and the mixture is heated under reflux. 0.725 ml of hydrazine hydrate are added slowly and reflux is continued for 24 hours. After cooling the mixture is filtered and the filtrate is evaporated. The residue is partitioned between sodium-EDTA-solution (0.25M; pH 9–10) and dichloromethane. The organic phase is evaporated to give 0.45 g of the title compound as a yellowish solid of m.p. 187–188° C. The mass spectrum shows the molecular peak MH+ at 264.2 Da.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux
  3. temperaturereflux
  4. temperatureAfter cooling the mixture
  5. filtrationis filtered
  6. customthe filtrate is evaporated
  7. customThe residue is partitioned between sodium-EDTA-solution (0.25M; pH 9–10) and dichloromethane
  8. customThe organic phase is evaporated

Sources & evidence

ORD record
ord-6addb36814c74a7b9b850bf5bca5e634
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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