Ethanol → 4-Chloro-2-methoxy-5-(1-methylcyclopropyl)aniline

HRID 588870Notes

Reaction equation

HRID 588870 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2([CH3:11])[CH2:10][CH2:9]2)=[CH:6][C:5]([NH:12]C(=O)C)=[C:4]([O:16][CH3:17])[CH:3]=1.[OH-].[K+].C(O)C>O>[Cl:1][C:2]1[C:7]([C:8]2([CH3:11])[CH2:9][CH2:10]2)=[CH:6][C:5]([NH2:12])=[C:4]([O:16][CH3:17])[CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 90455914N-[4-Chloro-2-methoxy-5-(1-methylcyclopropyl)phenyl]acetamide

Product 1

HCID 904558234-Chloro-2-methoxy-5-(1-methylcyclopropyl)anilineYield 67.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-(4-chloro-2-methoxy-5-(1-methylcyclopropyl)phenyl)acetamide (820 mg, 3.23 mmol), KOH (1.8 g, 32.3 mmol), ethanol (40 mL) and water (20 mL) was stirred at reflux for 12 h. The reaction mixture was extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=20:1) to afford the desired product (460 mg, 67% yield). ESI-MS m/z: 212.4[M+H]+.

Workup

  1. temperatureat reflux for 12 h
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washThe combined organic layer was washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=20:1)

Sources & evidence

ORD record
ord-0056386f1ecc487cbeac5491d8ced0cf
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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