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

HRID 839444Notes

Reaction equation

HRID 839444 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-3,5-dinitrotoluene (9.0 gm.) 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., ,.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., ,.p. 114°-115.5°, 70% yield)

Sources & evidence

ORD record
ord-79948550b6a04b6b8f626e6bc8e9378d
Source dataset
uspto-grants-1978_06
Patent number
US04095028

Reaction notes

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