Hydrochloric Acid → 4-Chloro[1,1'-biphenyl]-3-amine

HRID 652263Notes

Reaction equation

HRID 652263 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[N+:14]([O-])=O.Cl.[Sn]>C(O)C>[NH2:14][C:3]1[CH:4]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 137921574-Chloro-3-nitro-1,1'-biphenyl

Product 1

HCID 126208214-Chloro[1,1'-biphenyl]-3-amineYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 62.0 g (0.266 mole) of 4-chloro-3-nitro-biphenyl, 400 ml of concentrated hydrochloric acid and 100 ml of absolute ethanol was heated at reflux while 93 g (0.785 mole) of 20 mesh granular tin metal was added in portions over a 1 hr period. Heating was continued for 2 hr. The white slurry which resulted was cooled and filtered. The white precipitate (filter cake) was partitioned between dilute sodium hydroxide and methylene chloride. The methylene chloride layer was dried over magnesium sulfate and concentrated under reduced pressure to give a solid residue. Recrystallization of the residue from cyclohexane gave 47.5 g (88%) of the title compound as white powder, m.p. 91.0°-92.5° C.

Workup

  1. temperaturewas heated
  2. additionwas added in portions over a 1 hr period
  3. temperatureHeating
  4. customThe white slurry which resulted
  5. temperaturewas cooled
  6. filtrationfiltered
  7. filtrationThe white precipitate (filter cake)
  8. customwas partitioned between dilute sodium hydroxide and methylene chloride
  9. dry with materialThe methylene chloride layer was dried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customto give a solid residue
  12. customRecrystallization of the residue from cyclohexane

Sources & evidence

ORD record
ord-ef29c85215c146ebb434a56639da9bb0
Source dataset
uspto-grants-1987_06
Patent number
US04670566

Reaction notes

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