Water → N1,N1-Dimethyl-N3-(4-nitrophenyl)-1,3-propanediamine

Temperature

150 °C

34. In a 125 mL flask were mixed 14.11 g. (0.10 mole) of 4-fluoronitrobenzene, 10.22 g. (0.10 mole) of 3-(dimethylamino) propylamine and 5.00 g. (0.12 mole) of dry sodium fluoride. Upon warming, a reaction began, and after an hour the mixture was heated to 150° C. for an hour. The mixture was cooled below 100° and treated with 400 mL water containing 0.10 mole sodium hydroxide at 60° C. for one hour; it was then chilled to solidify the freed amine and the aqueous phase was decanted off. After three water washings and drying, the crude product was dissolved in methyl tertiary butyl ether, filtered and evaporated to dryness, giving 19.69 g. (88% yield) of N-(3-dimethylaminopropyl) 4-nitroaniline, m.p. 60°-61.5° C. A 2.23 g. (0.01 mole) portion of this product was dissolved in 15 mL of acetone and treated with 2.13 g. (0.015 mole) of methyl iodide in a closed vessel. There was an immediate reaction and presently a yellow solid was suddenly precipitated. The mixture was warmed for 1/2 hour at 50° C. cooled, filtered, washed with acetone, and dried; the remaining solid, weighing 3.31 g., m.p. 210°-211.5° C., represented a 90% yield of Dye No. 34.

1. addition34. In a 125 mL flask were mixed 14.11 g
2. temperatureUpon warming
3. temperatureThe mixture was cooled below 100°
4. temperatureit was then chilled
5. customthe aqueous phase was decanted off
6. dry with materialAfter three water washings and drying
7. dissolutionthe crude product was dissolved in methyl tertiary butyl ether
8. filtrationfiltered
9. customevaporated to dryness
10. customgiving 19.69 g

ORD record

ord-77c7b2a989304339a7324ad26a5a0a30

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05240780