3,4,5-Trimethoxybenzaldehyde → HCID 11460264, compound

HRID 505359Notes

Reaction equation

HRID 505359 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].[O-]S([O-])(=O)=O.[Mg+2].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25])[CH:19]=O>C(Cl)(Cl)Cl>[CH3:27][O:26][C:22]1[CH:21]=[C:18]([CH:17]=[C:16]([O:15][CH3:14])[C:23]=1[O:24][CH3:25])[CH:19]=[N:5][CH2:4][CH:3]([O:6][CH3:7])[O:2][CH3:1]

Participants

5

Reactant 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 11460264HCID 11460264, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Aminoacetaldehyde dimethylacetal (20.0 mL, 19.5 g, 0.185 mol) was dissolved in chloroform (80 mL) and MgSO4 (15 g) was added. Then 3,4,5-trimethoxybenzaldehyde (10c, 10.03 g, 0.05112 mol) was also added and the mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with chloroform (70 mL), washed with water (4×150 mL), brine (150 mL), dried (Na2SO4), and concentrated to provide the pure imine as a colorless oil (14.47 g, 100%). 1H NMR (300 MHz CDCl3) 8.10 (s, 1H), 6.91 (s, 2H), 4.58 (t, J=5.4 Hz, 1H), 3.81 (s, 6H), 3.79 (s, 3H), 3.69 (s, J1=5.4 Hz, J2=1.2 Hz, 2H), 3.33 (s, 6H).

Workup

  1. washwashed with water (4×150 mL), brine (150 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2a6332f7236a4bbaa3f003ccdc9b7b09
Source dataset
uspto-grants-2010_08
Patent number
US07781445B2

Reaction notes

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