Pyridine → N-(4'-chloro-1,1'-biphenyl-2-yl)acetamide

HRID 2181880Notes

Reaction equation

HRID 2181880 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([NH2:14])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16].N1C=CC=CC=1>CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][C:15](=[O:17])[CH3:16])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 2622612-Amino-4'-chlorobiphenyl

Product 1

HCID 22482266N-(4'-chloro-1,1'-biphenyl-2-yl)acetamideYield 51.1%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The title compound was prepared from 4′-chloro-1,1′-biphenyl-2-amine (3.5 g, 17.19 mmol), acetic anhydride (1.79 mL, 18.9 mmol), pyridine (3.2 mL, 39.5 mmol), and 4-(N,N-dimethylamino)pyridine (0.06 g, 0.52 mmol) according to the procedure and in the same manner as described in Example 60, step b. The crude product was purified by re-crystallization from a mixture of ethyl acetate-hexane to yield N-(4′-chloro-1,1′-biphenyl-2-yl)acetamide (2.16 g, 8.78 mmol, 51%) as a white solid;

Workup

  1. customThe crude product was purified by re-crystallization from a mixture of ethyl acetate-hexane

Sources & evidence

ORD record
ord-9d7f61c897f84f4c9e4c796566c0edcd
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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