3,4,5-Trimethoxybenzaldehyde → HCID 44633462, compound

HRID 388256Notes

Reaction equation

HRID 388256 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([CH:11]([O:16][CH3:17])[C:12]([NH:14][NH2:15])=[O:13])[CH:9]=[CH:10][C:2]1=2.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH:23]=O>C(O)C.C(O)(=O)C.CCOCC>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([CH:11]([O:16][CH3:17])[C:12]([NH:14]/[N:15]=[CH:23]/[C:22]3[CH:25]=[C:26]([O:30][CH3:31])[C:27]([O:28][CH3:29])=[C:20]([O:19][CH3:18])[CH:21]=3)=[O:13])[CH:9]=[CH:10][C:2]1=2

Participants

6

Reactant 2

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 59185914HCID 59185914, compound

Product 1

HCID 44633462HCID 44633462, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

In a round-bottom glass flask equipped with a magnetic stir bar 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-methoxyacetohydrazide (1 eq., 1.1 mmol; 260 mg) was dissolved in ethanol (10 mL) at room temperature. To this well stirred solution, acetic acid (˜3 drops) and 3,4,5-trimethoxy-benzaldehyde (1.2 eq, 1.3 mmol; 260 mg) were added, and the reaction mixture was heated for 12 hours. The mixture was then cooled and the crude product was diluted with Et2O and filtered and the solid was washed thoroughly with Et2O to yield: 300 mg (65%) of (2-1).

Workup

  1. temperaturethe reaction mixture was heated for 12 hours
  2. temperatureThe mixture was then cooled
  3. filtrationfiltered
  4. washthe solid was washed thoroughly with Et2O to yield: 300 mg (65%) of (2-1)

Sources & evidence

ORD record
ord-1dcbd35905e34d8c85251315af88c691
Source dataset
uspto-grants-2013_02
Patent number
US08377930B2

Reaction notes

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