Formaldehyde → Methyl N-methylanthranilate

HRID 1249616Notes

Reaction equation

HRID 1249616 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH2:12]=O.[H][H]>[Pd].C(OCC)(=O)C>[CH3:12][NH:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 8635Methyl AnthranilateHCID 178418361HCID 178418361, compound

Product 1

HCID 6826Methyl N-methylanthranilate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

In a 5 gallon Star autoclave was placed methyl anthranilate (6.65 lbs, 20 mol), ethyl acetate (7000 mL) and K-10 powder (300 g). The mixture was cooled to 5° C. Then a 37% aqueous formaldehyde solution (1,600 mL, 21.2 mol) and 5% palladium on carbon catalyst (300 g) were added. The mixture was then hydrogenated at room temperature for 20 hours at an initial hydrogen pressure of 150 psi with continuous stirring. The mixture was filtered, and the solvent was evaporated at reduced pressure. The residue was distilled through a packed column (24×2") to provide methyl N-methylanthranilate b2.0 110° C. as a colorless liquid. Yield: 7.02 lbs (96.5% of theor.). GLC purity: 99%.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated at reduced pressure
  3. distillationThe residue was distilled through a packed column (24×2")

Sources & evidence

ORD record
ord-d62273fc366340a6a3419be900c5416f
Source dataset
uspto-grants-1986_12
Patent number
US04633009

Reaction notes

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