Ethanol → 2,6-Dichloro-3,5-dimethoxyaniline

HRID 912549Notes

Reaction equation

HRID 912549 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[NH:13]C(=O)C.CCO.[OH-].[K+]>O>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[NH2:13]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 56594869N-(2,6-dichloro-3,5-dimethoxyphenyl)acetamide

Product 1

HCID 594862532,6-Dichloro-3,5-dimethoxyaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of N-(2,6-Dichloro-3,5-dimethoxy-phenyl)-acetamide 15 (6.50 g, 24.61 mmol) in mixture of EtOH (80 mL) and water (30 mL), is added KOH (20 g) and stirred 2 days at 80° C. After the solvent (EtOH) is removed on vacuum, water (˜15 mL) is added, a white solid is collected by filtration and washed with water, dried to give final product 16: 1H NMR 600 MHz (CDCl3) δ 6.03 (s, 1H), 4.55 (s, 2H), 3.88 (s, 6H); MS m/z 222.00 (M+1).

Workup

  1. customAfter the solvent (EtOH) is removed on vacuum, water (˜15 mL)
  2. additionis added
  3. filtrationa white solid is collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-6d06e9a29f3743f6bd7dc7dc17c6ee2a
Source dataset
uspto-grants-2011_09
Patent number
US08026243B2

Reaction notes

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