HCID 68157084, compound → 3-Methyl-N2-phenyl-1,2-benzenediamine

HRID 242769

Reaction equation

HRID 242769 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCOC(C)=O.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 68157084HCID 68157084, compound

Product 1

HCID 681571473-Methyl-N2-phenyl-1,2-benzenediamineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2-methyl-6-nitrophenyl)phenylamine (981 mg, 4.3 mmol) and 10% Pd/C (981 mg) in EtOAc (20 mL) was degassed with a stream of nitrogen and then stirred at RT under a hydrogen atmosphere for 4 h. The suspension was then filtered through a PTFE frit and the filtrate was concentrated in vacuo affording 3-Methyl-N2-phenylbenzene-1,2-diamine as a yellow solid (852 mg, 100%). LCMS: RT 3.02 min [M+H]+ 199.0

Workup

  1. customwas degassed with a stream of nitrogen
  2. filtrationThe suspension was then filtered through a PTFE frit
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e489c1a362ac4d40849bb7ad10509aba
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Linked notes

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