HCID 10609383, compound → HCID 10535968, compound

HRID 242812Notes

Reaction equation

HRID 242812 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([N+:15]([O-])=O)[CH:3]=1>CCOC(C)=O.[Pd]>[CH3:1][C:2]1[CH:3]=[C:4]([NH2:15])[C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 10609383HCID 10609383, compound

Product 1

HCID 10535968HCID 10535968, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (4-methyl-2-nitrophenyl)phenylamine (1.41 g, 6.18 mmol) and 10% Pd/C (140 mg) in EtOAc (30 mL) was degassed with a stream of nitrogen and stirred at RT under a hydrogen atmosphere for 5 h. The suspension was then filtered through a PTFE frit and the filtrate was concentrated in vacuo affording 4-Methyl-N1-phenylbenzene-1,2-diamine as an off-white solid (1.18 g, 96%). LCMS: RT 3.08 min [M+H]+ 199.1.

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-8a2115b491984758b2da01cd2c700221
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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