Methylamine → HCID 178482641, compound

HRID 493480Notes

Reaction equation

HRID 493480 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]=O)=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH3:18][NH2:19].[O-]S([O-])(=O)=O.[Mg+2]>C(O)C.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13](/[CH:16]=[N:19]/[CH3:18])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 576816103'-Bromo-4'-methoxy-1,1'-biphenyl-4-carbaldehyde

Product 1

HCID 178482641HCID 178482641, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3′-bromo-4′-methoxy-1,1′-biphenyl-4-carbaldehyde (7.56g, 26.0 mmol), prepared in the previous step, methylamine (16.2 mL of an 8.03 M solution in ethanol; 130 mmol) and 20.0 g of anhydrous MgSO4 in 150 mL of methylene chloride was stirred under nitrogen at room temperature for 22 h. The reaction was filtered and the filtrate concentrated under reduced pressure to give N-[(E)-(3′-bromo-4′-methoxy-1,1′-biphenyl-4-yl)methylidene]-N-methylamine (7.77 g, 98%) as a brown solid, mp 115-117° C. Elemental Analysis for C15H14BrNO. Calc'd: C, 59.23; H; 4.64; N, 4.60. Found: C, 58.99; H, 4.38; N, 4.63

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-d9b704a77ab6412ea95a5bbdcdb5b2c4
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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