4-Nitroaniline → HCID 86743147, compound

HRID 1904809Notes

Reaction equation

HRID 1904809 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:11]([C:14]1[CH:19]=[CH:18][N+:17]([O-:20])=[CH:16][CH:15]=1)([O-:13])=[O:12]>CC(C)=O>[N+:11]([C:14]1[CH:19]=[CH:18][N+:17]([O-:20])=[CH:16][CH:15]=1)([O-:13])=[O:12].[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 74754-Nitroaniline2×HCID 143004-Nitropyridine N-oxide

Product 1

HCID 86743147HCID 86743147, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A saturated solution of 4-nitroaniline was made by heating 50 ml of acetone to boiling in a beaker on a hot plate and adding 4-nitroaniline with stirring until no more of the added solid dissolved. A saturated solution of 4-nitropyridine-N-oxide was made using the same method. About 25 ml of each saturated solution was filtered and subsequently mixed together. A solution of soapy water was made to use as a surfactant layer. A thin (1-2 mm) layer of 50%/50% v:v of soap and water solution was pipetted onto the top of the solution to prevent wicking of the solution up the sides of the beaker. The surfactant layer was used to improve the quality of crystals and does not affect the composition of the final product. The solution was left undisturbed for five days until crystals of 2 were isolated. The crystals of 2 were clear, bright red, and shaped like sword blades. The approximate size of these crystals was 2.00 mm×0.20 mm×0.05 mm. The melting point of a single crystal of 2 was 124.0-126.0° C.

Workup

  1. dissolutiondissolved
  2. filtrationAbout 25 ml of each saturated solution was filtered
  3. additionsubsequently mixed together
  4. customwere isolated
  5. customwas 124.0-126.0° C.

Sources & evidence

ORD record
ord-3dd96c9108e94f6f869e9b483bf11d13
Source dataset
uspto-grants-1989_06
Patent number
US04839536

Reaction notes

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