Veratraldehyde → 39964-87-9

HRID 505352Notes

Reaction equation

HRID 505352 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].[O-]S([O-])(=O)=O.[Mg+2].[CH:14](=O)[C:15]1[CH:24]=[CH:23][C:20]([O:21][CH3:22])=[C:17]([O:18][CH3:19])[CH:16]=1>C(Cl)(Cl)Cl>[CH3:19][O:18][C:17]1[CH:16]=[C:15]([CH:24]=[CH:23][C:20]=1[O:21][CH3:22])[CH:14]=[N:5][CH2:4][CH:3]([O:6][CH3:7])[O:2][CH3:1]

Participants

5

Reactant 3

HCID 8419VeratraldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 1125379939964-87-9

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Aminoacetaldehyde dimethylacetal (11 mL, 10.73 g, 0.102 mol) was dissolved in chloroform (50 mL) and MgSO4 (8.5 g) was added. Then veratraldehyde (10a, 9.22 g, 0.055 mol) was added and the mixture was stirred at room temperature. After 24 h the MgSO4 was filtered out and the filtrate was washed with water (200 mL), brine (200 mL), dried (Na2SO4) and concentrated to provide the imine, a light yellow liquid (13.90 g, 100%). 1H NMR (300 MHz, CDCl3) δ8.09 (s, 1H), 7.33 (d, J=1.8 Hz, 1H), 7.07 (dd, J1=1.8 Hz, J2=8.3 Hz 1H), 6.77 (d, J=8.1, 1H), 4.57 (t, J=5.1 Hz, 1H), 3.83 (s, 3H), 3.80 (s, 31H), 3.65 (dd, J1=5.1 Hz, J2=1.2 Hz, 2H), 3.32 (s, 6H).

Workup

  1. filtrationAfter 24 h the MgSO4 was filtered out
  2. washthe filtrate was washed with water (200 mL), brine (200 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d9924b22468947f4b67cc444e63e2298
Source dataset
uspto-grants-2010_08
Patent number
US07781445B2

Reaction notes

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