Potassium Carbonate → N-(1,3-dioxolan-5-ylmethyl)-2-methyl-6-methoxyaniline

HRID 596746Notes

Reaction equation

HRID 596746 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:3]=1[NH2:4].Cl[CH2:12][CH:13]1[O:17][CH2:16][O:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CC)(CC)CC)C>[O:17]1[CH:13]([CH2:12][NH:4][C:3]2[C:5]([O:9][CH3:10])=[CH:6][CH:7]=[CH:8][C:2]=2[CH3:1])[CH2:14][O:15][CH2:16]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2401534-(Chloromethyl)-1,3-dioxolaneHCID 4592492-Methoxy-6-methylaniline

Product 1

HCID 21447805N-(1,3-dioxolan-5-ylmethyl)-2-methyl-6-methoxyaniline

Reagents, catalysts & solvents 1

HCID 5946Tetraethylammonium ChlorideCatalyst

Procedure

2-Methyl-6-methoxyaniline (0.3 mole), 5-chloromethyl-1,3-dioxolane (0.3 mole), potassium carbonate (0.3 mole) and tetraethylammonium chloride (2 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is heated at reflux for a period of 4 hours. After this time the mixture is filtered and distilled to yield the desired product N-(1,3-dioxolan-5-ylmethyl)-2-methyl-6-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 4 hours
  5. filtrationAfter this time the mixture is filtered
  6. distillationdistilled

Sources & evidence

ORD record
ord-6c3dd6d9ae0242c2a9e4310cff0e2f25
Source dataset
uspto-grants-1977_03
Patent number
US04012222

Reaction notes

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