Dichloromethane → 2-Aminobiphenyl

HRID 2181824Notes

Reaction equation

HRID 2181824 reaction equation
I[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:9][O:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=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][O:10][C:11]1[CH:16]=[C:15]([C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[NH2:4])[CH:14]=[CH:13][CH:12]=1.[C:2]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:3]([NH2:4])=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 119952-IodoanilineHCID 14798Sodium HydroxideHCID 2734370(3-Methoxyphenyl)boronic acid

Product 2

HCID 70152-AminobiphenylYield 197.5%HCID 2759560SBB007488

Reagents, catalysts & solvents 1

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

Procedure

3′-Methoxy-1,1′-biphenyl-2-ylamine was prepared from 2-iodoaniline (3.64 g, 16.7 mmol), 3-methoxyphenylboronic acid (2.54 g, 16.7 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (0.41 g, 0.50 mmol), and a 5 N aqueous sodium hydroxide solution (6.7 mL, 33.5 mmol), according to the procedure and in the same manner as described in Example 32, Method A, Step a, to afford the intermediate biphenyl amine as an oil (2.79 g, 84%). The title compound was prepared from the above intermediate biphenyl amine (0.75 g, 3.8 mmol), acetic anhydride (1.4 mL, 15 mmol), 4-(N,N-dimethylamino)pyridine (0.05 g, 0.4 mmol), and pyridine (1.2 mL, 15 mmol) according to the same procedure as described in Example 32, Method A, Step a to yield N-(3′-methoxy-1,1′-biphenyl-2-yl)acetamide as a solid (0.60 g, 66%), m.p. 105-107° C.;

Sources & evidence

ORD record
ord-a414dcfbe1214a2fb12e16cd15e45620
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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