4-Amino-3-methyl-5-nitrobiphenyl → 3,4-Diamino-5-methylbiphenyl

HRID 452173Notes

Reaction equation

HRID 452173 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][C:3]=1[CH3:17]>C(OCC)(=O)C.CCCCCC.[C].[Pd]>[NH2:8][C:7]1[CH:6]=[C:5]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:4]=[C:3]([CH3:17])[C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 672105084-Amino-3-methyl-5-nitrobiphenyl

Product 1

HCID 672110583,4-Diamino-5-methylbiphenylYield 100%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

[step 3] 4-Amino-3-methyl-5-nitrobiphenyl (100 mg, 0.44 mmol) obtained in step 2 was dissolved in ethanol-ethyl acetate (1/1, 4 mL), and the mixture was stirred in the presence of 10% palladium carbon (10 mg) under a hydrogen atmosphere at room temperature for 20 hr. The mixture was filtered, and the filtrate was concentrated under reduced pressure to give 3,4-diamino-5-methylbiphenyl (87 mg, 100%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a589cb4c60034c0e83cfb1ce936b1176
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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