Pyridine → HCID 11345498, compound

HRID 1080608Notes

Reaction equation

HRID 1080608 reaction equation
N1C=CC=CC=1.Cl.[CH3:8][NH:9][O:10][CH3:11].[C:12]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13]([C:18](Cl)=[O:19])=[CH:14][CH:15]=[CH:16][CH:17]=1>ClCCl.C(OCC)(=O)C>[CH3:11][O:10][N:9]([CH3:8])[C:18]([C:13]1[C:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:19]

Participants

6

Reactant 3

HCID 1049PyridineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 12563768[1,1'-Biphenyl]-2-carbonyl chloride

Product 1

HCID 11345498HCID 11345498, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The intermediate N-methoxy-N-methyl-p-biphenylcarboxamide was first formed. Pyridine (4 mL, 5 equivalents) and N,O-dimethylhydroxylamine hydrochloride (980 mg, 10 mmol) were added to a solution of p-biphenylcarbonyl chloride (2.16 g, 10 mmol) in dry dichloromethane (10 mL). The solution was stirred for 2 hours at room temperature and then diluted with ethyl acetate (20 mL), washed sequentially with 1N HCl (2×20 mL), saturated sodium bicarbonate (20 mL), and brine (20 mL). It was then dried over magnesium surfate and evaporated under reduced pressure to give N-methoxy-N-methyl-p-biphenylcarboxamide as a solid (1.78 g, 74%). The solid was recrystallized from ethyl acetate/hexane for analysis: mp 77°-78° C. The identity of the solid was confirmed as that of N-methoxy-N-methyl-p-biphenylcarboxamide by IR, proton NMR, 13C NMR and elemental analysis, with mass spectrometric determination of the molecular weight.

Workup

  1. washwashed sequentially with 1N HCl (2×20 mL), saturated sodium bicarbonate (20 mL), and brine (20 mL)
  2. dry with materialIt was then dried over magnesium surfate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c565d8caa84f465487a400c6fc1afbcf
Source dataset
uspto-grants-1996_12
Patent number
US05583000

Reaction notes

Loading…