Ethanol → 4-Bromo-2,6-dichloro-3-methylaniline

HRID 974411Notes

Reaction equation

HRID 974411 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([Br:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[NH:11]C(=O)C.C(O)C.[OH-].[Na+]>O>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([Br:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[NH2:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 110146Acetamide, N-(4-bromo-2,6-dichloro-3-methylphenyl)-

Product 1

HCID 150272334-Bromo-2,6-dichloro-3-methylanilineYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution consisting of 2.07 g of N-(2,6-dichloro-4-bromo-3-methylphenyl)acetamide, 50 mL of ethanol, 25 mL of water and 25 mL of 50 percent NaOH were refluxed until hydrolysis was complete. The reaction mixture was cooled and extracted with ethyl ether. The extract was washed with water, dried over MgS04 and filtered. Removal of the solvent under reduced pressure gave 1.6 g of white solid. The product was purified by elution with pentane from a silica gel column and recrystallization from heptane (m.p. 67-69° C). 1H NMR (CCl4) δ7.33 (s, 1H), 4.40 (s, 2H, NH2), 2 40 (s, 3H, CH3).

Workup

  1. temperaturewere refluxed until hydrolysis
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ethyl ether
  4. washThe extract was washed with water
  5. customdried over MgS04
  6. filtrationfiltered
  7. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-62a3108f7e4c4b5684a28037ab1e4285
Source dataset
uspto-grants-1991_11
Patent number
US05068392

Reaction notes

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