Methyl iodide → N-Methyl-o-phenylenediamine

To one liter of methanol were added 89 grams (0.82 mole) of o-phenylenediamine and 25.7 ml. (0.41 mole) of methyl iodide. The mixture was refluxed for 2 hours, and an additional 25.7 ml. (0.41 mole) of methyl iodide then were added. The total mixture was refluxed for 12 hours. The major portion of the methanol then was removed in vacuo. The residual brown oil was poured into two liters of crushed ice, and the pH of the mixture was raised to 9.0 by addition of potassium hydroxide. The resulting mixture then was extracted with ethyl ether, and the extract was dried over potassium carbonate. The ether was removed in vacuo, and the residue was distilled at about 120° C./8 mm. to obtain N-methyl-o-phenylenediamine as a yellow oil which turned brown upon standing.

1. temperatureThe mixture was refluxed for 2 hours
2. temperatureThe total mixture was refluxed for 12 hours
3. customThe major portion of the methanol then was removed in vacuo
4. additionThe residual brown oil was poured into two liters of crushed ice
5. temperaturethe pH of the mixture was raised to 9.0 by addition of potassium hydroxide
6. extractionThe resulting mixture then was extracted with ethyl ether
7. dry with materialthe extract was dried over potassium carbonate
8. customThe ether was removed in vacuo
9. distillationthe residue was distilled at about 120° C./8 mm

ORD record

ord-79fd753d3e8a430cb7406d6aa1d19f3b

Source dataset

uspto-grants-1977_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04061861