Hydrochloric Acid → N-{4'-methyl-[1,1'-biphenyl]-2-yl}acetamide

HRID 2181877Notes

Reaction equation

HRID 2181877 reaction equation
[CH3:1][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.[Cl-].[NH4+].Cl>ClCCl.CN(C1C=CN=CC=1)C>[CH3:1][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

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 25517Ammonium ChlorideHCID 15108204'-Methyl-biphenyl-2-ylamine

Product 1

HCID 12915287N-{4'-methyl-[1,1'-biphenyl]-2-yl}acetamideYield 83.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 4′-methyl-1,1′-biphenyl-2-amine (3.09 g, 16.87 mmol) in dichloromethane was treated with acetic anhydride (1.75 mL, 18.6 mmol), pyridine (3.14 mL, 38.8 mmol), and 4-(N,N-dimethylamino)pyridine (0.062 g, 0.506 mmol). After stirring under argon for 16 hours, a saturated, aqueous, ammonium chloride solution (5 mL) was added to the reaction mixture and stirring continued another 30 minutes. The reaction mixture was poured into a 0.1 N hydrochloric acid solution. The separated aqueous phase was further extracted with dichloromethane (3×). The combined organic phase was washed sequentially with a 0.1 N hydrochloric acid solution and a saturated aqueous, sodium bicarbonate solution. After drying over anhydrous magnesium sulfate, the solvent was removed in vacuo. The crude product was purified by re-crystallization from a mixture of ethyl acetate-hexane to yield the title compound (3.17 g, 14.1 mmol, 83%) as a white, crystalline solid;

Workup

  1. stirringstirring
  2. waitcontinued another 30 minutes
  3. extractionThe separated aqueous phase was further extracted with dichloromethane (3×)
  4. washThe combined organic phase was washed sequentially with a 0.1 N hydrochloric acid solution
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customThe crude product was purified by re-crystallization from a mixture of ethyl acetate-hexane

Sources & evidence

ORD record
ord-803de6f54f894a24a24e38b753c501ac
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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