Methane → 4'-Methyl[1,1'-biphenyl]-3-amine

HRID 1455619Notes

Reaction equation

HRID 1455619 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=2)=[CH:4][CH:3]=1.C.O.NN>C(O)(C)C.[Fe](Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 297MethaneHCID 24654Hydrazine hydrate (1:1)HCID 6435234'-Methyl-3-nitro-1,1'-biphenyl

Product 1

HCID 12621544'-Methyl[1,1'-biphenyl]-3-amineYield 95%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
65 °C

Procedure

4′-Methyl-3-nitro-biphenyl (1.9 g) dissolved in isopropyl alcohol (30 mL) and iron (III) chloride (0.19 g) added followed by charcoal (0.19 g). Mixture heated to 65° C. before adding hydrazine hydrate (7.6 mL) slowly for 45 minutes under nitrogen. Mixture stirred for a further 2 hours at 70° C. Mixture filtered and washed with ethyl acetate. Organics combined and washed with water (50 mL) and brine (50 mL) before drying over sodium sulfate, filtering and evaporating to dryness to leave a yellow solid (1.55 g, 95%).

Workup

  1. filtrationMixture filtered
  2. washwashed with ethyl acetate
  3. washwashed with water (50 mL) and brine (50 mL)
  4. dry with materialbefore drying over sodium sulfate
  5. filtrationfiltering
  6. customevaporating to dryness

Sources & evidence

ORD record
ord-ffc45f04301a4c7489ddec3377a07a16
Source dataset
uspto-grants-2009_01
Patent number
US07482469B2

Reaction notes

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