Formaldehyde → Methyl N-methylanthranilate

HRID 1249615Notes

Reaction equation

HRID 1249615 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, compound2×

Product 1

HCID 6826Methyl N-methylanthranilate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

In a 2 L Parr pressure reactor was placed methyl anthranilate (302 g, 2.0 mol), ethyl acetate (700 mL), K-10 powder (30 g) and 5% palladium on carbon catalyst (30 g). The mixture was cooled to 5° C. and 37% aqueous formaldehyde solution (160 mL, 2.12 mol) was added. The mixture was then hydrogenated at room temperature at an initial hydrogen pressure of 50 psig with continuous stirring. After hydrogen uptake had ceased (7 h), the mixture was filtered through filter-aid. The filtrate was dried and the solvent was evaporated at reduced pressure. The residue was distilled through a Vigreaux column (30×2 cm) to provide methyl N-methylanthranilate, b12.0 130°-132° C. as a colorless liquid. Yield: 317 g (96% of theor.). GLC purity: 99.7%.

Workup

  1. custom(7 h)
  2. filtrationthe mixture was filtered
  3. filtrationthrough filter-aid
  4. customThe filtrate was dried
  5. customthe solvent was evaporated at reduced pressure
  6. distillationThe residue was distilled through a Vigreaux column (30×2 cm)

Sources & evidence

ORD record
ord-d178b90daa39490a858a965b22091a5f
Source dataset
uspto-grants-1986_12
Patent number
US04633009

Reaction notes

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