Hydrochloric Acid → 4,6-Dichlorobenzene-1,3-diamine

HRID 236937

Reaction equation

HRID 236937 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[C:6]([N+:10]([O-])=O)=[CH:5][C:4]=1[N+:13]([O-])=O.[OH-].[Na+]>>[NH2:13][C:4]1[C:3]([Cl:2])=[CH:8][C:7]([Cl:9])=[C:6]([NH2:10])[CH:5]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 772861,3-Dichloro-4,6-dinitrobenzene

Product 1

HCID 33728694,6-Dichlorobenzene-1,3-diamine

Procedure

To a solution of 399 gm. (1.77 mole) of stannous chloride dihydrate in 975 ml. of concentrated hydrochloric acid is added 60 gm. (0.258 mole) of 1,5-dichloro-2,4-dinitrobenzene. The temperature rises to 72° and a solution occurs. The mixture is allowed to cool to room temperature and then cooled in an ice-bath (to 5°). A cold 50% solution of sodium hydroxide is added, with cooling, until the mixture is strongly basic. The mixture is filtered and the precipitate on the funnel washed four times with 500 ml. portions of ethyl acetate. The ethyl acetate extracts are combined, dried over anhydrous M9SO4 and the solvent removed. The residue is recrystallized from 50% ethanol-water. There is obtained 31.9 gm. (70%) of colorless needles melting at 142-3°.

Workup

  1. customrises to 72°
  2. temperaturecooled in an ice-bath (to 5°)
  3. temperaturewith cooling, until the mixture
  4. filtrationThe mixture is filtered
  5. washthe precipitate on the funnel washed four times with 500 ml
  6. customdried over anhydrous M9SO4
  7. customthe solvent removed
  8. customThe residue is recrystallized from 50% ethanol-water
  9. customThere is obtained 31.9 gm

Sources & evidence

ORD record
ord-cf0fbddac1074383a6b5e63e410f16e2
Source dataset
uspto-grants-1979_06
Patent number
US04159278

Linked notes

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