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

HRID 28045Notes

Reaction equation

HRID 28045 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])[CH2:20][O:19]1>>[CH3:23][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

Participants

4

Reactant 3

HCID 70002-MethoxyanilineHCID 10340Sodium CarbonateHCID 141307cis-2-Bromomethyl-4-methyl-1,3-dioxolane

Product 1

HCID 23338376N-(4-methyl-1,3-dioxolan-2-ylmethyl)-2-methoxyaniline

Conditions

Temperature
100 °C

Procedure

2-Methoxyaniline (99 grams; 0.6 moles) and sodium carbonate (31.6 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. 2-Bromomethyl-4-methyl-1,3-dioxolane (25 ml) was added and the reaction mixture was heated at a temperature of about 100° C. for a period of about 4 hours. After this time the reaction mixture was filtered and additional sodium carbonate (5.0 grams) was added to the filtrate. The mixture was then vacuum distilled and the fraction boiling at 120° C. and 0.07 mm of Hg pressure was collected to yield the desired product N-(4-methyl-1,3-dioxolan-2-ylmethyl)-2-methoxyaniline.

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 (5.0 grams) was added to the filtrate
  5. distillationvacuum distilled
  6. customthe fraction boiling at 120° C. and 0.07 mm of Hg pressure was collected

Sources & evidence

ORD record
ord-e99f9d76b08a481ba3c31cb20e20a62f
Source dataset
uspto-grants-1980_09
Patent number
US04225335

Reaction notes

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