N-(2,6-dichloro-3,5-dimethoxyphenyl)acetamide → 2,6-Dichloro-3,5-dimethoxyaniline

HRID 58124Notes

Reaction equation

HRID 58124 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+]>[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

4

Reactant 1

HCID 56594869N-(2,6-dichloro-3,5-dimethoxyphenyl)acetamide

Product 1

HCID 594862532,6-Dichloro-3,5-dimethoxyanilineYield 76%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N-(2,6-dichloro-3,5-dimethoxy-phenyl)-acetamide (3.6 g, 13.7 mmol) in EtOH (130 mL) and KOH (2M, 75 mL) was heated to reflux for 24 hours. The reaction was cooled to 0° C. and stirred for 1 hour at this temperature. The precipitate was filtered and dried to obtain the title compound (2.3 g, yield: 76%). 1H-NMR (400 MHz, CDCl3) δ 3.90 (s, 6H), 4.57 (bs, 2H), 6.05 (s, 1H).

Workup

  1. temperatureto reflux for 24 hours
  2. filtrationThe precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-db93a3e73ce646a1818d8569692e8d1a
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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