2-Methoxyaniline → HCID 23338370, compound

HRID 28039Notes

Reaction equation

HRID 28039 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]([CH2:23][CH2:24][CH3:25])[CH2:20][O:19]1>>[CH2:23]([CH:21]1[CH2:20][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)[CH2:24][CH3:25]

Participants

4

Reactant 3

HCID 70002-MethoxyanilineHCID 10340Sodium CarbonateHCID 233383912-Bromomethyl-4-propyl-1,3-dioxolane

Product 1

HCID 23338370HCID 23338370, 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-propyl-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-propyl-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-24d24d89ab8b4c48a8a7cd14df8e53d6
Source dataset
uspto-grants-1980_09
Patent number
US04225335

Reaction notes

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