2,3,4-Trimethoxybenzaldehyde → HCID 11448955, compound

HRID 505364Notes

Reaction equation

HRID 505364 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH:5]=O.COC1C=C(C=CC=1OC)C=[N:21][CH2:22][CH:23]([O:26][CH3:27])[O:24][CH3:25]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH:5]=[N:21][CH2:22][CH:23]([O:26][CH3:27])[O:24][CH3:25]

Participants

4

Reactant 2

HCID 750062,3,4-TrimethoxybenzaldehydeHCID 1125379939964-87-9

Product 1

HCID 11448955HCID 11448955, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2,3,4-Trimethoxybenzaldehyde (10e, 11.48 g, 0.05851 mol) was dissolved in benzene (200 mL) and aminoacetaldehydedimethylacetal (10.0 mL, 9.75 g, 0.0927 mol) was added. The same procedure was applied as for 11a. The product was isolated as a clear light yellow oil (16.58 g, 100%), bp 153-155° C. (0.45 mm Hg). 1H NMR (300 MHz CDCl3) 8.49 (s, 1H), 7.64 (d, J=8.7 Hz, 1H), 6.65 (d, J=8.7 Hz, 1H), 4.61 (t, J=5.4 Hz, 1H), 3.88 (s, 3H), 3.84 (s, 3H), 3.82 (s, 3H), 3.71 (d, J=5.4 Hz, 2H), 3.36 (s, 6H); low resolution ESIMS m/z (rel intensity) 284 (MH+, 100), 252 (45). Anal. Calcd for C14H21NO5: C, 59.35; H, 7.47; N, 4.94. Found: C, 59.67; H, 7.55; N, 4.88.

Workup

  1. additionaminoacetaldehydedimethylacetal (10.0 mL, 9.75 g, 0.0927 mol) was added

Sources & evidence

ORD record
ord-3e0e75b21f4345d5b526dbae43b37953
Source dataset
uspto-grants-2010_08
Patent number
US07781445B2

Reaction notes

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