2-Methoxyaniline → HCID 23338371, compound

HRID 28041Notes

Reaction equation

HRID 28041 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]([CH2:24][CH3:25])[O:19]1>>[CH3:23][CH:21]1[CH:20]([CH2:24][CH3:25])[O:19][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:22]1

Participants

4

Reactant 3

HCID 70002-MethoxyanilineHCID 10340Sodium CarbonateHCID 23338392HCID 23338392, compound

Product 1

HCID 23338371HCID 23338371, compound

Procedure

2-Methoxyaniline (0.05 mole) and sodium carbonate (30 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. 2-Bromomethyl-4-methyl-5-ethyl-1,3-dioxolane (0.55 mole) is slowly added and the reaction mixture is heated at reflux for a period of about 1 hour. After this time the reaction mixture is filtered and additional sodium carbonate (5 grams) is added to the filtrate. The mixture is then distilled under reduced pressure to yield the desired product N-(4-methyl-5-ethyl-1,3-dioxolan-2-ylmethyl)-2-methoxyaniline.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperaturethe reaction mixture is heated
  4. temperatureat reflux for a period of about 1 hour
  5. filtrationAfter this time the reaction mixture is filtered
  6. additionadditional sodium carbonate (5 grams) is added to the filtrate
  7. distillationThe mixture is then distilled under reduced pressure

Sources & evidence

ORD record
ord-7ba03b475b164844814c4ec69b455bef
Source dataset
uspto-grants-1980_09
Patent number
US04225335

Reaction notes

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