2-Methoxyaniline → N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-2-methoxyaniline

HRID 28034Notes

Reaction equation

HRID 28034 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:17][CH:18]1[O:22][CH:21]([CH3:23])[CH:20]([CH3:24])[O:19]1>>[CH3:24][CH:20]1[CH:21]([CH3:23])[O:22][CH:18]([CH2:17][NH:5][C:4]2[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=2[O:2][CH3:1])[O:19]1

Participants

4

Reactant 3

HCID 70002-MethoxyanilineHCID 10340Sodium CarbonateHCID 128944572-Bromomethyl-4,5-dimethyl-1,3-dioxolane

Product 1

HCID 23338386N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-2-methoxyaniline

Conditions

Temperature
100 °C

Procedure

2-Methoxyaniline (87 ml; 0.7 mole) and sodium carbonate (31.66 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. 2-Bromomethyl-4,5-dimethyl-1,3-dioxolane (25 mls) was added and the reaction mixture was heated at a temperature of 100° C. for a period of about 4 hours. After this time the reaction mixture was filtered and additional sodium carbonate (5.00 grams) was added to the filtrate. The mixture was then distilled under reduced pressure to yield the desired product N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-2-methoxyaniline boiling at 125° to 128° C. at 0.1 mm of Hg pressure.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. filtrationAfter this time the reaction mixture was filtered
  4. additionadditional sodium carbonate (5.00 grams) was added to the filtrate
  5. distillationThe mixture was then distilled under reduced pressure

Sources & evidence

ORD record
ord-b450100da9fe427db4334b43432f4259
Source dataset
uspto-grants-1980_09
Patent number
US04225335

Reaction notes

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