Dichloromethane → 2-Aminobiphenyl

HRID 2181838Notes

Reaction equation

HRID 2181838 reaction equation
I[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][CH:15]=1.ClCCl.[OH-].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:9][C:10]1[CH:15]=[C:14]([C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[NH2:4])[CH:13]=[CH:12][CH:11]=1.[C:2]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:3]([NH2:4])=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 119952-IodoanilineHCID 14798Sodium HydroxideHCID 27339503-Tolylboronic acid

Product 2

HCID 70152-AminobiphenylYield 179.5%HCID 15108182-(3-Methylphenyl)aniline

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

3′-Methyl-1,1′-biphenyl-2-ylamine was prepared from from 2-iodoaniline (2.97 g, 13.5 mmol), 3-methylphenylboronic acid (1.84 g, 13.5 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (0.33 g, 0.41 mmol), and a 5 N aqueous sodium hydroxide solution (5.4 mL, 27 mmol), according to the procedure and in the same manner as described in Example 32, Method A, Step a, to afford the intermediate biphenylamine as an oil (2.05 g, 83%). The title compound was prepared from the above intermediate biphenylamine (1.89 g, 10.3 mmol), propionic anhydride (2.64 mL, 20.6 mmol), 4-(N,N-dimethylamino)pyridine (0.12 g, 1.0 mmol), and pyridine (3.3 mL, 41 mmol), according to the same procedure, to yield N-(3′-methyl-1,1′-biphenyl-2-yl)propanamide as a solid (2.45 g, 99%), m.p. 83° C.;

Sources & evidence

ORD record
ord-1e3da74e94a54639831fb590e6223dff
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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