Methane → HCID 21882732, compound

HRID 722058Notes

Reaction equation

HRID 722058 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]([Cl:18])=[C:14]([Cl:19])[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:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 24654Hydrazine hydrate (1:1)HCID 16768649HCID 16768649, compound

Product 1

HCID 21882732HCID 21882732, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.051 g of ferric chloride and 0.085 g of activated charcoal are added to a suspension of 0.35 g of 2-amino-5-(3,4-dichlorphenyl)-3-nitropyridine (starting material G2) in 10 ml of methanol and the mixture is heated under reflux. 0.270 ml of hydrazine hydrate are added slowly and reflux is continued for 12 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 0.20 g of the title compound as a yellowish solid of m.p. 202–204° C. The mass spectrum shows the molecular peak MH+ at 254.2 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-dd60c2f398bd4d8481441cd27970600b
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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