3,4,5-Trimethoxybenzaldehyde → 42864-53-9

HRID 1438834Notes

Reaction equation

HRID 1438834 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=O.[C:15]([CH2:17][C:18]([NH2:20])=[O:19])#[N:16].N1CCCCC1>N1C=CC=CC=1>[C:15]([C:17](=[CH:6][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=1)[C:18]([NH2:20])=[O:19])#[N:16]

Participants

5

Reactant 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 7898CyanoacetamideHCID 8082Piperidine

Product 1

HCID 30487042864-53-9Yield 92.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

100 g of 3,4,5-trimethoxy-benzaldehyde and 44 g of α-cyano-acetamide were dissolved in 300 cc of dry pyridine at 50°. To this solution 10 cc of piperidine were added and the mixture was heated at 50° with stirring for 2 hours. The reaction mixture was cooled at room temperature, filtered off and the precipitate was washed on the filter with 50 cc of cold isopropanol. The product was dried at 80° to yield 123.6 g (92.5%) of α-cyano-3,4,5-trimethoxy-cinnamamide; m.p. 192°-194°. This product was used for the hydrogenation step without further purification. A pure sample, recrystallized from isopropanol, melted at 193°-195°.

Workup

  1. temperaturethe mixture was heated at 50°
  2. filtrationfiltered off
  3. washthe precipitate was washed on the
  4. filtrationfilter with 50 cc of cold isopropanol
  5. customThe product was dried at 80°

Sources & evidence

ORD record
ord-193b742c759a4f46b9689d5acd0278c3
Source dataset
uspto-grants-1977_11
Patent number
USRE029467

Reaction notes

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