Aniline → 2-Methyl-N-phenylaniline

HRID 1596161Notes

Reaction equation

HRID 1596161 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C>[NH:9]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 72362-Bromotoluene

Product 1

HCID 109869462-Methyl-N-phenylaniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Bromotoluene (2 mmol) is heated to 230° C. for 6 hours with aniline (20 mmol) in the presence of [(C6H5)2PCH2]2Ni(CO)2 (0.2 mmol) using ethanol (1.2 mL) as the solvent in a sealed tube to form 2-anilinotoluene. 2-Anilinotoluene is oxidized with potassium permaganate in water to form 2-anilinobenzoic acid. (See Cramer, et al., J. Org. Chem. (1975), 40:2267).

Sources & evidence

ORD record
ord-07c40535f777432385c5a62347134168
Source dataset
uspto-grants-2001_09
Patent number
US06291442B1

Reaction notes

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