3-Hydroxybenzaldehyde → HCID 17862086, compound

HRID 2109322Notes

Reaction equation

HRID 2109322 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10]([OH:16])(=[O:15])[CH2:11]C(O)=O.C(O)(=O)C.[CH3:21][NH2:22]>C(O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:5]([NH:22][CH3:21])[CH2:11][C:10]([OH:16])=[O:15])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 176Acetic AcidHCID 867Malonic AcidHCID 6329Methylamine

Product 1

HCID 17862086HCID 17862086, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Hydroxybenzaldehyde (25.7 g, 210 mmol) was dissolved in ethanol (70 ml), and malonic acid (25.7 g) and the acetic acid salt of methylamine (38.6 g) were added to the solution. The resulting mixture was heated under reflux for 3 hours. Crystals which precipitated in the reaction mixture were collected by filtration to afford the desired compound (24.1 g).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customCrystals which precipitated in the reaction mixture
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-30aba6d34bc846e48f98b641064ad82e
Source dataset
uspto-grants-2009_04
Patent number
US07514475B2

Reaction notes

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