(4-Nitrophenyl)hydrazine → HCID 67617986, compound

HRID 1600170Notes

Reaction equation

HRID 1600170 reaction equation
CO[CH:3]=[CH:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1.[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][NH2:21])=[CH:16][CH:15]=1)([O-:13])=[O:12]>C(O)C.Cl>[N+:11]([C:14]1[CH:15]=[CH:16][C:17]([NH:20][N:21]=[CH:3][CH2:4][C:5]2[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=2)=[CH:18][CH:19]=1)([O-:13])=[O:12]

Participants

5

Reactant 2

HCID 3310889(4-Nitrophenyl)hydrazineHCID 54529674HCID 54529674, compound

Product 1

HCID 67617986HCID 67617986, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 3-(2-EZ-methoxyethenyl)pyridine (3.43 g) in ethanol (15 ml) and 2N hydrochloric acid (25 ml) was heated under reflux for 1 hour and then cooled. 4-nitrophenylhydrazine (3.89 g) was added portionwise with stirring to give a solution which deposited a yellow solid. The mixture was cooled in ice and the solid was filtered off, washed with isopropanol,ether and then dried to give the title compound (5.32 g), m.p. 212°-214° C. Found: C,53.54; H,4.51; N,19.00. C13 H12N4O2 requires: C,53.34; H,4.48; N,19.14%.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperaturecooled
  3. customto give a solution which
  4. temperatureThe mixture was cooled in ice
  5. filtrationthe solid was filtered off
  6. washwashed with isopropanol,ether
  7. customdried

Sources & evidence

ORD record
ord-2eda3517fef247fb87e811c777d6374d
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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