Dichloromethane → [1,1'-Biphenyl]-3-amine, 5-methyl-

HRID 530376Notes

Reaction equation

HRID 530376 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.ClCCl>C(OCC)(=O)C.C(O)(=O)C.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:3]=1

Participants

6

Reactant 2

HCID 6344DichloromethaneHCID 536524073-Methyl-5-nitrobiphenyl

Product 1

HCID 11819709[1,1'-Biphenyl]-3-amine, 5-methyl-

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pd/C (10 wt %, 161 mg, 0.151 mmol) was added to a solution of 3-methyl-5-nitrobiphenyl (322 mg, 1.51 mmol) in ethyl acetate (10 mL) and acetic acid (1 mL). The reaction mixture was stirred under an atmosphere of H2 (balloon) for 3 hours and then dichloromethane (5 mL) was added. The reaction mixture was filtered through CELITE, washed with ethyl acetate and concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes) provided 5-methylbiphenyl-3-amine as a brown oil. 1H NMR (400 MHz, CDCl3) δ 7.58 (d, J=7.6 Hz, 2H), 7.43 (t, J=7.6 Hz, 2H), 7.34 (t, J=7.3 Hz, 1H), 6.85 (s, 1H), 6.75 (s, 1H), 6.55 (s, 1H), 2.35 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through CELITE
  2. washwashed with ethyl acetate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6660b0e9455a466d99a4267d5e3a19d1
Source dataset
uspto-grants-2016_05
Patent number
US09353066B2

Reaction notes

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