Methanol → 4-Chloro-2-fluoro-5-(1-methoxyethyl)aniline

HRID 231417Notes

Reaction equation

HRID 231417 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]([O:10][CH3:11])[CH3:9])=[CH:6][C:5]([NH:12]C(=O)C)=[C:4]([F:16])[CH:3]=1.[OH-].[K+].CO>O>[Cl:1][C:2]1[C:7]([CH:8]([O:10][CH3:11])[CH3:9])=[CH:6][C:5]([NH2:12])=[C:4]([F:16])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 14501808N-[4-chloro-2-fluoro-5-(1-methoxyethyl)phenyl]acetamide

Product 1

HCID 145018094-Chloro-2-fluoro-5-(1-methoxyethyl)anilineYield 118.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 0.6 g (0.0024 mole) of N-[4-chloro-2-fluoro-5-(1-methoxyethyl)phenyl]acetamide, 0.14 g (0.0025 mole) of potassium hydroxide, 10 ml of water, and 10 ml of methanol was heated at reflux for 24 hours. This mixture was cooled and diluted with 50 ml of water. The resulting mixture was extracted successively with methylene chloride and diethyl ether. The combined extracts were dried, filtered, and the solvent was evaporated under reduced pressure, leaving 0.58 g of 4-chloro-2-fluoro-5-(1-methoxyethyl)aniline as an oil. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. temperatureThis mixture was cooled
  4. extractionThe resulting mixture was extracted successively with methylene chloride and diethyl ether
  5. customThe combined extracts were dried
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8bdbf13b0c8c48598a1bb61c57d39141
Source dataset
uspto-grants-1989_07
Patent number
US04846875

Reaction notes

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