Hydrochloric Acid → 2-Chloro-5-methylbenzene-1,3-diamine

HRID 2052601Notes

Reaction equation

HRID 2052601 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([CH3:11])=[CH:4][C:3]=1[N+:12]([O-])=O.Cl.[OH-].[Na+]>C(O)C>[NH2:12][C:3]1[CH:4]=[C:5]([CH3:11])[CH:6]=[C:7]([NH2:8])[C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 789184-Chloro-3,5-dinitrotoluene

Product 1

HCID 124029792-Chloro-5-methylbenzene-1,3-diamineYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4-chloro-3,5dinitrotoluene (9.0gm.) is dissolved in 50% ethanol (30 ml.). Electrolytically reduced iron powder (14.2 gm.) is added and the stirred reaction mixture heated to reflux. Concentrated HCl (1 ml.) in 50% ethanol (5 ml.) is added dropwise and refluxing continued for one hour. The reaction mixture is allowed to cool slightly and made basic (pH 8) with 20% NaOH, then the iron removed by filtration. The filtrate is taken to dryness under reduced pressure and the residue extracted with hot Skellysolve "B" (700 ml.). The product precipitates in long needles that were collected by filtration (4.57 gm., m.p. 114--115.5°, 70% yield).

Workup

  1. customthe stirred reaction mixture
  2. temperatureheated to reflux
  3. temperaturerefluxing
  4. temperatureto cool slightly
  5. customthe iron removed by filtration
  6. extractionthe residue extracted with hot Skellysolve "B" (700 ml.)
  7. customThe product precipitates in long needles that
  8. filtrationwere collected by filtration (4.57 gm., m.p. 114--115.5°, 70% yield)

Sources & evidence

ORD record
ord-d27d6b584a8e423e9eae3d4dfabfa17a
Source dataset
uspto-grants-1980_01
Patent number
US04186127

Reaction notes

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